The Three Questions with Andy Richter - Tim Herlihy

Episode Date: July 15, 2025

Writer and comedian Tim Herlihy, who wrote or co-wrote many of Adam Sandler’s biggest films, including "Billy Madison," "Happy Gilmore," and "The Wedding Singer," joins Andy Richter to discuss meeting Sandler on their first day of college, pivoting from accounting to comedy, working on "Saturday Night Live," and his work on the long-awaited "Happy Gilmore" sequel (out July 25th on Netflix)!Do you want to talk to Andy live on SiriusXM’s Conan O’Brien Radio? Tell us your favorite dinner party story - leave a voicemail at 855-266-2604 or fill out our Google Form at BIT.LY/CALLANDYRICHTER. Listen to "The Andy Richter Call-In Show" every Wednesday at 1pm Pacific on SiriusXM's Conan O'Brien Channel.

Hey everybody, welcome back to The Three Questions. I'm your host, Andy Richter, and today I'm talking to Tim Hurley. Tim is a very well established, well known writer and comedian. He formerly was on Saturday Night Live as a writer and he's written or co-written many of Adam Sandler's films, including Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy, Grown Ups 2, and Hubie Halloween. I spoke with Tim while he was in town doing the final edit of Happy Gilmore 2,

which he co-wrote and produced with Adam Sandler. The film will be available to stream on Netflix starting July 25th. Here's my conversation with Tim Hurley. Well, Tim, I'm so glad you're here. This is, you know, you, a shoe LA at every turn. You look down your nose at this town. Yeah, keep going. It's not all true so far.

No, I mean, do you, how do you, I mean, you have never lived here. I've never lived here. You've obviously worked here a bunch. You know what? I think that was the issue is that I associated with work. Yeah, yeah. And it was never leisure out here.

But then my daughter went to UCLA. So that was the first time I was out here for non-work purposes. And I kind of saw it through new eyes. And I'm like, this is actually kind of nice. Yeah, yeah, it's not bad. But she graduated, so I'm back to all work. Oh, right, right.

What did she study there? I'm not sure. It's something about computers and statistics. We used to, in our day, that majors were one word, like accounting or math, and now it's like computational science. Once you said computers, I'm like, oh yeah, I wouldn't. She could explain it to me 10 times

and I'd forget it 10 times. I think math is in there. Yeah, yeah. One of the nine words. But that's funny that she chose UCLA to do math. Yeah. I mean, is she still here or did she move back? She moved to Wisconsin actually.

Oh wow. Yes, she's in the Midwest working in software development. Oh, that's awesome. Love it. That's awesome, yeah. Wisconsin's great. So you're out here editing Happy Gilmore 2. Yes, the second one.

Yeah, and what was that like to revisit? Cause that was, was that the first or was Billy Madison the first? Yeah, Billy Madison was the first. Yeah, yeah. And then, and then Happy Gilmore's second. Yeah. So it was like. But still this is really going back.

Yes, no, it's, I mean, sadly a lot of the cast has passed away. Oh wow. Yeah, like Bob Barker. Oh yeah, right. And then, you know, we actually lost Carl Weathers and Joe Flaherty, you know, while during production. Wow. You know, so the first thing I wrote before I just had

the inspiration to write a scene of Chubbs Pearson, which is Carl Weathers character in heaven and just wrote that and was so excited to get, he was such a great guy. Yeah, yeah. And getting to work with him again. And then he actually passed away while we were working on the script.

Yeah, I got to, and I've told this story before, but in the later Arrested Developments, I was teamed up with him and James Lipton from Inside the Actor Studio. We did a bunch of stuff together because I don't even remember. I think Bateman's character is pitching a show that involves the three of us. And so I worked with him on a few of these things, and he was playing himself and I was playing myself.

And as I've said previously, when you play yourself on Arrested Development, you are an asshole and a loser. Like, that's like, you name a person on that show that played themselves and in some way they're like a fuck up and an idiot and a loser. And I actually asked him once because there was there was this running gag of everyone seeing him and thinking he was another actor

and then being disappointed that it was Carl Weathers. And I was like, how do you feel about that? And he's like, it's not great. He's like, it's not, cause I'm used to it. You know, I'm used to getting picked on and being around people that I know like me, but they're shitting on me. And he's like, I know they like me and I like working here.

He goes, but it's, it is weird. And I was like, yeah, that's sorry about that. That's- It's funny cause he, you know, he played Apollo Creed, which is, you know, you know, and then in our movie, but he was a real alpha guy in person. Like he was not a second banana at all. He was just, he was very much an alpha kind of a,

a guy, people, a natural leader kind of a guy. Yes, yes. But yeah, great guy. Yeah. Well, that's a shame. Yes, yes. But yeah, great guy, yeah. Well, that's a shame. Well, and then you had to adjust, I imagine. Yeah, yeah, yeah. Yeah, yeah, yeah. That scene, yeah.

Right, didn't use AI? No, I guess. We didn't have the money for that. Didn't have the budget for that. We had to DH sail it for a couple of scenes. That was millions. And is it, I mean, does it, to go back and revisit the characters in the story, I mean,

is it like, do you have to, like, do you remember a lot of the stuff that you can go back and make sure you're not doubling over on the bits or something? Well, I mean, I feel like we've learned a lot since then. I think back to the me who wrote that with Adam, and I didn't know what I was doing. I was, you know, we had just done Billy Madison and kind of, you know, poured our heart and soul into that. And then they said, you want to do another movie? And I was, we were like, yeah, sure.

Like we had wasted every good idea on Billy Madison. So Adam was, you know, like 30 years of good or halfway good idea. So we were like, all right, well, maybe we'll do about a golf movie. Okay, yeah, why not? Like they just sort of fumbling we were like, all right, well, maybe we'll do about a golf movie. Okay, yeah, why not? Like they just sort of fumbling through and like, you know, I mean, I almost envy like the lack of overthinking

and just kind of like, okay, let's do that. Okay, that sounds good. All right, Bob Parker, sure. Okay. And now having to scheme and plot and lay in bed at night and think, do we're doing the right thing? Right.

So it was kind of fun to be back in that space. Yeah, I think you're right. I think it is true, like when you're younger, things are simpler because you don't understand all the complications that are going on. And it also, it's true too. You know, you go from one movie and you're sort of like, oh shit, have I used it all up?

And then it's like, oh, golf movie. Because then there's a bunch of scenes that just write themselves. Yeah, yeah, sports movies, yeah. There's a template there, you know. On the Conan Show, I always felt like whenever we went on the road, whether it was like Comic-Con or the Apollo Theater, or even if like went to Dallas

for a week, it's like the show got to be about something other than itself and then there were just all the you know like Dallas like JFK bits you know cuz those are funny or you know our cowboy shit or whatever when you talk about about doing Billy Madison and then worrying that like that was all you had. Like you weren't meant for this. You kind of set out to do something else. And in fact, started doing something else.

Yeah, no, this was all, you know, I was a business major. I was Sandler's roommate. And I helped him with writing in school because we kind of all did. Like, it was just sort of like, hey, I'm gonna go on stage and do some jokes. And so like, oh, here's a good joke for you. And like he would do, you know, but it was very much,

it didn't even qualify as a hobby. It was just sort of a thing. I had a cool roommate. Because he was your roommate. Yeah, yeah, why not? And he was assigned. It wasn't like you guys found each other, right? Yeah, no, complete, yeah.

Wow. Random, life-changing decision by the NYU housing office. What was he studying? Acting. He was a full-on like Lee Strasburg acting. Wow, and they put actors in with accounting students? Yeah, it was sick. That's just asking for trouble.

Yeah, there was no Facebook or whatever to pick. They would just like pick names and, hey, you're living together. Now, because like for me too, I read your story or just sort of the points of your life where you start out on one track and then you end up in show business and working with Adam and getting to work with all these.

You know, I mean, cause also it's like you're in another situation similar to what I'm in where you're just like working with the same funny, hilarious people all the time. And it's really fun. And like, you feel like you're cheating somehow. And, or at least that's how I feel. But when I, I'm like, oh, thank God,

she didn't have to go into accounting. Like that's what I take away from it. And I just wonder, cause like your dad was a fireman and I'm just wondering like, what were you thinking? Like, did you like accounting? Did you like math or were you just kind of doing something that you felt like was a sensible solid thing to do? You know, I didn't mind it.

I did, I did like, I have like a statistical part of me that enjoyed, you know, making balance sheets, balance and stuff like that. I didn't like work so much. I didn't like having to put a suit on and go to work. So I ended up going to law school, which was a pure three year dodge to avoid work. But then of course you have to work after that. And now you have student loan

or like additional student loan debt. So it becomes more important to get a job at that point. So, and that also was like something I felt like I could have done. so it becomes more important to get a job at that point. And that also was like something I felt like I could have done. I probably was a better accountant than I was a lawyer. Cause lawyers, you gotta have a certain, like we'd have to look through boxes of documents.

And I'm just like, they're probably fine. You know what I mean? Yeah. I skimmed them. Yeah, I got the gist. Right, right, right. It was fine. Yeah, and there's also like a performance aspect

to being a lawyer sometimes, you know? Yeah. I mean, are you comfortable with performing? I mean, you've had done kind of cameo roles and things and stuff. I've become comfortable, but you know, when I did that Mark Twain thing with Adam, it was like, I just wasn't nervous and I don't know why,

because I've been always nervous with public speaking and if I have to give a speech at the Boy Scouts for the Pinewood Derby or something, I'd be nervous. But like, I don't know why. Especially because you don't have a kid in the Boy Scouts. Yeah, no, exactly. There was people like, who are you? What the fuck is he doing here?

Put your shirt back on. But yeah, there's something about that. I don't know, maybe it's an age thing or just something. I just walked out and like, there was thousands of people and I just was like, I'm just gonna talk. And so I've become more comfortable over the years. Yeah, it definitely does help. Well, what now, cause you start, you go to NYU and then,

like, I'm just curious, like, what are the first days of being Adam Sandler's roommate like? Well, you know, I thought he was an upperclassman because he seemed so confident. Yeah. And his mother was there and she was decorating the room and I thought, why did they put me with an upperclassman? That's so weird.

Wow. And then we said, we went to go get our student IDs. He had to give his date of birth to the person, and it was that day, it was his birthday. And I was the type of person, if it was my birthday, you'd know within five minutes, like it's my birthday, by the way. They could tell from the crown that you'd be wearing.

Yeah, yeah. He had waited like three hours to tell me it was his birthday. So I was like, this is a cool customer here. This is a formidable person. You know, he's got some, but yeah, it was just, it was so much, it never laughed as hard. Just the cafeteria and just the pranks

and it just was a circus. And we sort of, he pulled other acting students who were nuts into the orbit. So my social life was really just came right to my dorm room. Like I just sat there on my bed and just watched the circus come to town. Why do you think he had that sort of poise?

Is that just natural or had he been performing at that point? Not really, he'd gone up, I think once in Boston and then, but hadn't- Cause I know he did it young, you know, he started young. Yeah, but really it was, and I think it was more sophomore year than freshman year. I think freshman year was just sort of

taking the acting classes and hanging out in the dorm. And then he really got serious about it. And then it was really, sophomore year was sort of the village clubs around NYU. And then junior year was kind of, he did a lot of road gigs out in New Jersey, Queens, Long Island. And then senior year years when he finally broke

into the city clubs, a comic strip and catch a rising star. So that was his college experience. Yeah, yeah. Now, were you a funny guy before? Like were you known as a funny guy? Were you a class clown or anything like that? I mean, I thought I was funny.

It wasn't a ton of people thought I was funny. I was pretty quiet. Were you kind of an introvert? Yeah, very much. Oh really? Yes. Yeah, yeah. Quiet in school and just sort of an observer and a quiet dude.

Are you still that way or do you think that your life is kind of the same way that, you know, going on stage after all this experience, you're sort of more outgoing? I don't think so. I think you can still be an introvert and be a performer or be out there like, and she did the job to do.

You know what I mean? Like, oh, now I have to do this. Like I couldn't, I don't think I'd be like a studio executive or something or something where I have to go. Even when I was a lawyer, I was like, I was doing like deals and stuff and I wasn't like, they didn't let me see the client that much. I was sort of, you know, in the, like checking for typos. And I was not like deals and stuff and I wasn't like, they didn't let me see the client that much. I was sort of, you know, like checking for typos.

And I was not in the client procurement business. But like, I think just like anything, you just learn how to do it. And some people can be good for 10 minutes or get through a dinner or, you know, whatever they have to do socially. So when you went away, when you went away to law school, I imagine, I don't know what,

was Adam then on SNL or was he doing? I think when I was in law school, right after graduation, he moved to LA. He was there for a couple of years before he got, I think he got SNL when I was in my second year of law school and he came back and he lived on the Upper East Side and I lived on the Upper East Side so But he you know he poured I was you know busy doing law school stuff

And yeah, I was helping him a little with the sketches back then But he wasn't getting that much on and he was hired as a writer so he was writing his own Yeah, writing for other people too. Was law school in New York. Yes. I went to NYU. Oh, okay, so I was still in New York Yeah, and and he still kind hittin' you up. Were you ever like, hey man, I'm in fuckin' law school. Write your own sketches. No. No.

No. Law school's pretty easy after the first year. First year was very hard, but then the second, third year's pretty easy. Yeah, like you can fake it. Yeah, I wasn't making it down to class that much. From the every side to the village, it was like, should I get on the six now?

Yeah. Well, when do you start to, because then after that you get a job, you know, as an accountant or as like sort of legal No, I was a Wall Street lawyer. I was down on Wall Street. So it was financial kind of, yeah, yeah, financial law. Like, do you, are you ever thinking like,

well, this is just a placeholder until I end up in show business? Not really. And when does that happen? It was funny, it kind of creeped up on me because I was doing it and I never thought that I would be, I mean, I think I realized sort of soon that I wasn't gonna be a partner,

like I wasn't that good at being a lawyer. Really? Because of, yeah, I wasn't a detailed person with like documents and stuff like that. And that's what it takes? Yeah, I think to be good at it, you have to kind of love it. Like the same thing with accounting

or really anything. Like to really be elite, you have to love it. Yeah. And I shouldn't be saying this, because I don't want to be, what's the statute of limitation on malpractice? Malpractice. But like Adam started saying at a certain point, you know, he started there at the bottom himself and then when he got in the cast and you know, he said, I think I could get you

on SNL and this guy Jim Downey is going to read your stuff. And for a couple of years, I wrote sketches that I later found out Jim never wrote, never read. And then- Thanks, Jim. There was a point where I wrote sketches, I guess this is in fall of 93, and I found out in like November that he didn't write them. And I remember sitting, I'll never forget this, I sat in the Pearl Street Diner downtown

and I was eating lunch at three. Sometimes I'd eat lunch late because, you know, just so nobody was there. I could be antisocial and I heard- Really dig in, really get it all over your face. Exactly, yeah, I could get it all over. Yeah, no, just everything. And I heard, what's that Paul Simon song

that he sang, Dressed Like a Turkey, still crazy after all these years, which I always associate with, I sit down and I was like, I started getting choked up. I'm like, I'm never, I'm just gonna be a lawyer for you. What's that Paul Simon song that he sang, dressed like a turkey, still crazy after all these years, which I always associate with SNL. And I was like, I started getting choked up. I'm like, I'm just gonna be a lawyer for the rest of my life. And I never really had thought that I was,

I never had articulated in my head that I wanted to be anything other than a lawyer, but it was like, it felt like the dream had just died. And you didn't even know you were having the dream. Yeah, exactly. Yeah. Yeah. And, but then three months later, Adam got me a tryout at the show in March of 94.

Which means going in and... Guest writer, yes. Guest writer, okay. You joined the writing staff for two weeks. And because he was, he had enough for a pull, enough sort of pull at that point to make that happen. Or, yeah, yeah. I mean, I think it just, he just nagged the hell out

of Downey and Jim, you know, Jim was a real big fan of Adams. Still is, I think. Yeah. And so he trusted him to bring in. And he just told me, just do whatever Downey says and listen to everything Downey tells you. And that's what I did. And then I got the permanent job offer.

Yeah, well, probably even him not reading those, I would imagine you felt some kind of growth in writing those sketches over the two years just in sort of getting some poise in writing them. Don't you think? Yeah, well I also written some stuff that got on. Oh wow. Yeah, canteen boy was a neighbor of my wife's growing up.

So I worked on them with Adam. And obviously the sketches went through, you know, Jim rewriting it and all the other writers, they are pitching in on Thursday rewrites and everything. But I had sort of generated this character on SNL to impress my girlfriend at the time. Right, right. And so, and you know, the same way with standup jokes,

like when I saw him do one of my jokes and it got laughs, that was an enormous boost of confidence. When I saw a sketch that I had, a line I had written in a sketch, get a laugh on Saturday Night Live, I was like, I guess I can do this. Yeah, yeah. So I guess I was more confident in the submissions

that Jim didn't read, but. Yeah, and you had met your wife by that point. So she was there during the transition from lawyer to comedy person. How did she, like, did she like that? Cause I mean, cause you're going from, I can provide you with stability to you're like, hey, I might fuck it all up at any moment, you know?

You know, looking back on it, it was so crazy. Yeah, yeah. We got engaged in February and then I quit my job in April. Wow. And then in May, we went off to Toronto for three months to shoot Billy Madison. Wow.

And she didn't sign up for any of that. Yeah, yeah. And then we came back in October and got married. And I just thought, you know, I was just so consumed with my own journey at that point. Like, yeah, I'm on Saturday Night Live, or, ooh, I did a movie. Yeah, yeah, yeah.

Like, I forgot that I'm dragging this poor girl along with me. Well, was she okay with all that? I mean, was it exciting for her, or was she nervous about it? I don't, I wouldn't say excited. Like, she was- Are you never spoken up? Yeah, this is my cry for help in this podcast.

No, I don't think she, I wouldn't say she was unexcited. I think she would have liked me just as well if I stayed a lawyer. I'd like to think that. Like she is not one of these people who vicariously gets into show business. But I think she accepted it and thought, oh, this is a new track we're on.

Yeah, yeah. And I had no idea like how I was giving up sort of a steady job. I thought, oh, I'm gonna go on SNL, I'm gonna be a great comedy writer forever. And I realized in retrospect that I just got very lucky to still be, you know. Right, and this is 93, so you're,

cause you're 19 days older than me. Really? Yeah, I'm 19 days older than me. Really? Yeah. I'm October 28th, 1966. So that's your whatever. Best 19 days of my life. No, Andy. Finally, finally. No, Andy.

No, but I mean, in 93, what does that make you? The 27? So yeah, I think, I mean, it's the same thing with me on the Conan show. I was blissfully ignorant. Like they're like, what about the pressure? I'm like, what pressure? I, you know, and as I've said before,

I'd read in the paper as, you know, like we got such shitty reviews and it would be like, you know, dumb fat loser Andy Richter. And what I would take from that was, oh, I'm in the paper. Look there, I'm in the paper. It's called my name right. Yeah, so I can understand like when you're that young too, it's, you know, it's, you know, there's.

There's a level of dumbness that kind of, I mean, that definitely was dumb. And I think the dumbness went on until about, you know, maybe after big daddy was, yeah, yeah. I started thinking until about, you know, maybe after Big Daddy was right. I started thinking, hey, maybe I should take this a little more seriously. It was just a lot of, it's funny. I remember watching the first code and I think I was at SNL.

Was it 94? No, it was 93. It was September something, maybe 29th of 93. Yeah, I remember watching it. Cause I remember Robert used to, Spiegel used to do, he had the bit of the, he had submitted a couple of times at the show of the guy, the stagehand dancing to Phil Collins' song.

And then he did it on the first show. And I realized like, oh, now he has to come up with something else. Like it's done. And now there's another 5, know, 5,000 shows. And that's how I felt with Happy Gilmore. Like, oh, now we have to come up with, I did it. That joke that we thought was gonna be great.

It's out there, it's done. Now we gotta come up with something new. And it's like, I mean, I always thought that the daily grind of that, I couldn't have done it in a million years, worked on a show like that. Well, it's spread out over a bunch of people, but yeah, especially in the beginning,

part of the naivete of that time was not also not knowing. We felt like we just had to do as much as we possibly could and shove as much. We would put so much comedy into those early shows where we would interrupt interviews to do a little little quickie comedy bit which I mean nowadays is like what the fuck were we thinking like we just had a famous person there Talking just let him fucking talk. You don't have to you know, do graphics and costumes for a 45 second something, you know But yeah, it was it was the blissful ignorance too. And I mean, you get the job and then you gotta fucking do it.

You know, it's, you know. And I guess like after a year, like it must have been like, wow, okay. Yeah. This is a marathon. You just keep, I mean, there's all kinds of, you know, like when I put together a packet for that, I had been doing improv. I had never sat down and wrote a packet for a late night show. So, clickety-clack, here's a packet of sketch ideas. Then I'd go do things like Robert pushed me out to do

remotes because at the time there was this worry that if Conan did remotes, it would look too much like what Letterman did. So I was sort of like the other guy and could go out and do stuff and sent me to Mardi Gras. And like there was one of the things they set up was, you're gonna go to Little Richard's hotel suite and interview him.

And like, I had not taken any classes in college on how to interview Little Richard, you know? And so all of a sudden I'm fucking there having to- I had not taken any classes in college on how to interview Little Richard. You know? And so all of a sudden I'm fucking there having to interview Little Richard and you just kind of, you know, you figure it out as you go along. And I imagine there was a good amount of that, you know, because, you know, you have the, first of all, you have two hit movies, one after the other. And that's got to put a lot of pressure on you to keep going.

Or was it the sense that because you had Adam working with you and I imagine there's other people too, like, cause he's kind of had the same, you know, like Alan Covert and different people that have kind of been with him all along. Did you ever feel like, oh shit, I, you know, I gotta do this again. I mean, aside from just that first time?

Well, yeah, I mean, I think after, we had, the way we did it in the early days, we would be well into the next movie before the first movie came out. I see. So we couldn't really react to that. We kind of made the deal for the second movie. So a producer we worked with, Bob Simons,

said always make the deal for the next movie before the first movie comes out because in that case it's a bomb. Yeah, yeah, right, exactly. You'll have, Bob Simons, that always make the deal for the next movie before the first movie comes out because in the case it's a bomb, y'all have. So we were hard, by the time Billy came out, we were already well into Happy. And then by the time Happy came out, we were well into The Wedding Singer and The Waterboy. So like, it was definitely a growth.

It was more reacting not to the prior movie, but the movie before that. Right, right. So they didn't, yeah. So you can't even like go like, well, you know, Happy Gilmore is a big hit. So when was Wedding Singer next? Was that it?

Yeah, we did Billy Happy, Wedding Singer, and Waterboy. And they each did better than the one prior. Right, right. So, but you're just like, okay, let's, you know, you don't even have like the cockiness of like, this second one did better. You're sort of like, fingers crossed. Yeah, no, it's like, let's hope this does good

and we can stay in show business. Especially after Adam left SNL to shoot Happy Gilmore, there was a little bit of desperation that like even we understood in our dumbness that if this movie didn't do well, cause Happy didn't do great. I mean, I mean that if this movie didn't do well, because Happy didn't do great. I mean, sorry, Billy didn't do. Did 25 million at the bottom.

It was okay. Yeah. But nothing like it had sort of life after. It made money though, and that's the main thing. Yeah. Yeah, yeah. But it wasn't like a huge life-changing success. Yeah. So we just sort of, and it is traumatic to leave SNL

and there is like a little bit of pressure and so Adam had felt that. And same way I felt it when I left five years later. You did feel that? You know, I didn't think I would. I was certainly cocky, like, I don't need this show no more. You've already been doing all these hit movies. Yeah, I had hit movies, but then I was like nervous

and I just said yes to everything because I was just like, you know, I didn't have the security blanket of Santa Claus. Right, right. Yeah. What kind of prompted you to say no to SNL? I just, back in the day, that like five years was like plenty, you know, and that felt like the normal.

That's what Lorne did his first, you know, that whole crew was there for five years. And that was sort of, there were some people obviously, you know, who had long, you know, franken, but they were few and far between, you know, was very much sort of a in and out. You kind of did your, it was like, you know, college, you know, just do your bit.

And then at a certain point you're done. I actually went back for a sixth year, but then I was like, I kind of quit halfway through the year. I was like, no, this is a mistake. Was it the grind got to you too? Yeah, I had been writing movies and then doing the show and it just was, you know, having children. Yeah, that's what I was gonna say.

Did you have kids during that time? Yeah, I had my oldest in 98. And then, yeah, so, but really, the immediate thing that I quit the show was to work on Little Nicky. Yeah. Which I probably should have stayed at the show. I needed to devote my full attention to the biggest bomb of my career.

Well, it's probably in a way, healthy, to sort of have a little bit of a holistic approach. Like it's not all gravy. Like sometimes you got to take a hit. Yeah. I mean, that's part of life. There's no one when to leave and when to leave the party. And in every aspect of life, there's a time to move. There's a time to, and you never a time to, you know, and you just, you never

time it perfect, but you know, time it close. In those early days, and I think that, like what you guys were doing with these movies, Adam's movies, I mean, there are all of you guys's, but I movies, Adam's movies, I mean, they're all you guys's, but I mean, he's the star of it and he will not let you forget it. But with doing these movies, there was a similarity, I think, in some ways to like what we were doing early in late night, which is people liked it,

it's doing well, but but critics do not like it. And I don't know, there've been some brutal critics to Adam's movies and to the movies you guys wrote together. And I wonder if that just rolls off your back because they're so successful, or is there a part of you that like still kind of craves the validation of those fuckers?

I mean, it wasn't fun at the time. I mean, that's kind of a lost world now where like there's this weird, it's now been replaced by this other sort of zeitgeisty thing of- Right, you're on Netflix and who gives a shit. Internet lecture, you know what I mean? It's a weird thing.

But back then, yeah, there were important critics that, you know, when they would... Yeah, it was a little bit of a bummer because we thought we were, you know, doing great stuff. And then they would say, oh, you're so lazy and all that. Well, I know we're not lazy. We may suck, but I know we're not lazy. Ask my kid if I'm lazy, yeah.

Not sure what his name is. And so, yeah, I wouldn't say I craved it, but it would have been nicer if, you know, because it was always like one of the last things that happens in this journey. You write it, you come up with the idea, you write it, you shoot it, you edit it, and then it comes out and people shit all over it.

You know, and then it's like, oh, well, kind of had a bad ending to that little adventure. Yeah, yeah, yeah. So, you know, a lot of times we had the box office to kind of, you know, see with ourselves, you know. Right, oh, that makes a huge difference. Regular folks like it, you know what I mean? So, but yeah, a little bit, sure.

Yeah, wanting that, want everybody to like you. Did that help? Because you ended up nominated for Tonys for the book of the wedding singer and for musical and best, book of the musical and best musical. Well, the thing is, to be honest, there's only like 10 musicals come out a year

and four are bombs. So you got a good chance if it's not an absolute bomb. Oh, you totally could have been like, yes, I took the theater world by storm. Missed your chance. Yeah, I think that got nominated, yes, I took the theater world by storm. You missed your chance. Yeah, I think that got nominated, but that was a fun experience. Bro, it was a lot of fun, man. Yeah, yeah.

I bet it was, because it's also too, like, again, it's all brand new and exciting. And it's so much tradition and you're kind of walking down 42nd Street or whatever, like, hey, how you doing? See you Saturdays later. It's all kind of cool and show busy. I meant to ask earlier, I forgot, how did your folks feel about this journey? From going, like my boys in NYU studying accounting, oh, now he's in law school.

Now he's writing fart jokes. You know? You know? You know, I think it was so blurring. You know, it's just, you know, they were happy when I was an accountant. And that was like sort of, you know, my grandparents were Irish immigrants and they, you know,

they were farmers and then they came to this country and my father's father was a motor man in the subway. Oh, wow. And then his son was a fireman, which was like kind of a step up the ladder. Yeah. And then if son was a fireman, which was like kind of a step up the ladder. And then if I was an accountant, I would be doing my bit for the family ancestry to kind of the rise.

The advancements of the Irish people. Exactly. So I think when I went to law school, they were like, okay, like it wasn't on their radar of anybody, they didn't know any lawyers, like it just seemed. And then, so that kind of prepared them for the, oh, it's gonna be a comedy writer.

But then I got to be, because what happened to Santa Live was that I became a senior person very quickly, because after my first year, a lot of people left. It was sort of a big purge year. So I went from being the rookie to sort of a senior person there, my second year. So I was head writer by my third year.

And then my parents would come to the show and the pages would be like, oh, Mr. Hurley, how are you? And they were very, you know, they thought that that was like, oh, cool. So the time that they had to worry about me, I think was short. Yeah.

Were you comfortable getting to a position to tell people what to do? Because sometimes, you know, it's like, that's a thing where like when you go from being someone who's told what to do to then being the person that tells people what to do, and it can be a little daunting. Well, what was so good was that I had been, you know, Annapid told me, just do

whatever Downey says, watch Downey do what Downey does, like when I got the job. And that's what I kind of did is I followed Downey so that when I got, you know, his job, I kind of just tried to do what Downey would do. I kind of kept everything, whatever Downey did, I'll just do that and fake my way through it. And one of the things Downey did, which you never say you don't like something, like when people would bring me sketches

and some would be awful and I'd go, oh, let's get some good, and that was such good, it wasn't advice because I was more fun than what more fun doing, but I learned a lot from, from Jim. Yeah. Of how to get through that job. Yeah. It's hard though. And you know, Conan and I ended up, we were sort of like the final step in the quality control part of our show. And he, and it's one of the best things that he gave me was inviting me into like should we do this bit or not or how do we fix this bit kind of stuff and so over the years I got you know

I'd be I got producing skills basically but it was really hard where there'd be days where we'd be in the monologue meeting the band would be doing the warm-up, we'd be in his room and then a writer would come in with a bit that was shot and graphics and everything and we'd look at it. And I always felt like I was the hammer and I would go, uh-uh, no, I'm sorry, just, you know. And I would try, like I probably was not as good at it as I should have been in terms of going like, well, there's some nice things here.

But it's also because I was just like forged in the early days of the show where there was no time for feelings. You know what I mean? And when I came out here too, I was like a fucking asshole to everyone where they'd be like, you didn't laugh at that joke. And I'm like, yeah, I mean, it works, it's good,

but what do I gotta go, ha ha ha ha? But probably people didn't come to you with their problems because I kind of have a little of that with Salem. Like people, I can say that because I don't have to deal with the repercussions. People, when they're writers with hurt feelings would go to, you know, Robert or Conan or, you know, when you don't have to deal with the repercussions

of saying something's not funny, it's a lot easier. Right, right, right, exactly, exactly. Yeah, no, I, in ways I wish I had redone it, or done it differently, like, like had, but I, you know, but then again, I'm like. Somebody's gotta do it. Yeah. It's like, there's no universal right or wrong.

It's just gonna, it comes down to like, nah, it's judgment calls. And you need to just have a couple of people who get to say yes or no. And then just, like I said, move on. Our business is like generating too much material And then just, like I said, move on, you know, and not. We, our business is like generating too much material that we can't use at all and love to be fair about it. And like every writer on SNL gets this number

of sketches a year, but it doesn't, it's a little Darwinian and that's just the nature of it. And it's difficult too, because there is this sort of fine line between being invested in your stuff and like, I think this is funny and I'm going to do this and believing in yourself. But then also, like, if someone wants to kill your baby, you go, all right, I can always have another baby. You know, it's difficult because there is, you got to care, but then at a certain point, you have to stop caring. Yeah.

You have to cut your losses and move. Even this morning, looking at doing editing on Happy Gilmore 2, like I have my babies, I have my things that they don't kill, but I think that in 20 years, people will be putting them on t-shirts and having to make that argument, especially with the playback of the audience

with nobody laughing. And like they just hit play and they just see the stone faces. And I'm like, well, deep down, they're really, they're gonna laugh later, like when they think about that joke. Yeah. Well, and you do have to, you know, because I mean, I would come up with stuff on the show that I would think, oh man, this is so fucking funny.

And then I would go read it in front of everybody and be like, oh, I guess I was wrong. I guess I was wrong. Oh boy. Re-throws are great teachers. Yeah, yeah, yeah. Well, zigged when I should have zagged on that one, yeah. Now, I imagine, you know,

cause you all of your, you know, this sort of change in your life, you're all of a sudden thrown into like famous people, being around famous people, being around famous people. And I mean, were there, are there like early stories of that, that you can remember that were sort of like?

I mean, I think this has been consistent throughout is like someone who meant something to you as a kid. Yeah. I think there's something that resonates in you and just getting nervous and just being, cause you could meet the biggest stars out there. Like when I went to, I remember there was once I went out to LA, it was early, I was in the nineties

and I met Jim Carrey and I met Roseanne and I met kind of the big, huge stars of that day. And I'm not saying I wasn't a little intimidated but not that intimidated. And then on not saying I wasn't a little intimidated, but not that intimidated. And then on the plane home, I'm sitting there and Ralph Keiner gets on it. Ralph Keiner was the Mets announcer. And I had grown up listening to the sound of his voice.

And he was an old Pittsburgh pirate. And I was just, I almost started crying. I mean, it was just so like, oh my God, Ralph Keiner just walked past me and I got his autograph. Yeah, yeah. And, you know, I was actually a lawyer because that autograph said, good luck in the legal game. So I was just visiting Adam.

But I mean, I was so like, because he had meant something to me growing up. Yeah, yeah. And not that anything against Jim or Roseanne or, but that's- He was sitting further back in the plane than you, so. Yeah, no, that was, I felt, turned into satisfaction. Enjoy it back there, Ralph.

Enjoy, I'll send you back some peanuts. And Adam sort of has assembled this great group of people with him that he's, a lot of from SNL people to even like, when you go in the grownups movies, it's just basically, it's like, he just goes to speed dial on his phone and casts a movie. And does that make things easy for you? I mean, and do you end up getting relationships

with some of these people? Yeah, I mean, it's so nice to be able to do, like come up with a character and then a certain point, you're like, Steve Buscemi could play this character or John Tartaro could play this character. And just knowing how good it's going to be, how it's going to be elevated and just how cool and just getting to work with, I mean, I think I came into the business not having a lot of respect for actors. I just thought they were kind of, you know, as any writer, they're just meat

puppets who, you know, come in working, we're with Drew on Wedding Singer and just seeing that she elevated this stuff. And then Kathy Bates on Waterboy and just like, wow, that's better than I imagine. Cause you imagine in your head how great it's gonna be. And then it's almost never that good. But with certain actors, like it's better than you imagine. And like, how did they do that?

It's magical in many ways. Yeah, what did they do? What, what, how did they come up with that? Yeah, I did a, I did a, Will Arnett had a short-lived multi-camera sitcom and Margot Martindale played his mom. And, you know, before a multi-camera show, you get together and you do what they call a speed through,

which is where basically you just run through all the lines. And in this case, it was in the makeup room. You just do the whole show top to bottom real fast, just to make sure you all have the lines. And I was sitting next to Margot Martindale as she did her lines. And you know, it's a sitcom. It's not Shakespeare,

you know, it was a funny sitcom, but she's doing her lines like fast and not even putting any real spin on them or anything. And it was fucking compelling. I was just like, holy shit. Like that's, like she's amazing. And I like, I'm forgetting my lines because I'm so taken away by what she's amazing and I like I'm forgetting my lines because I'm so you know

taken away by what she's doing uh and it is it's just like kind of magical in that way and I mean Adam has that. Adam does stuff he's one of those people that does stuff that's just it's a different thing than an actor thing in that it's just oh my god uh, you know, as they say, read a, read a menu and it's funny, you know, and he does that, you know, there's so much stuff that if you, if you were to do like, you know, like the, uh, the closed caption transcribing of, of things that he does, it would be like, wait, makes a noise. It's like, Oh, okay. He made a noise.

Does that over and over? Yeah. Yeah. Yeah. Makes another noise. You know what I mean? It's like, oh, okay, he made a noise. Just that over and over. Yeah, yeah, yeah. Makes another noise. Yeah, yeah, exactly. So yeah. I mean, he's just done so much and then he goes off and does these sort of prestige kind of things with these great directors

and just can, you know, when I'm like, you're working with PTA or you're working with Noah Baumbach and like thinking he'd be intimidated and he just goes in and kills it. Yeah, yeah. Have you guys, has there ever been any sort of like rifts between you guys where you feel like, well, maybe we're gonna part ways

or has it always been pretty friendly and where there hasn't really been? There's never been any kind of rift at all. I mean, I think at a certain point, when I was fully in show business, I realized, like people are always gonna think of me as Adam Sandler's roommate, unless I go out and do some other thing.

I'm always just gonna be like, oh, this kid got lucky. And so, you know, and I've done a lot of other stuff, but none of it got made. But, you know, that was important to me for like five years, like other people don't just think of me as Adam Sandler's lucky college roommate. I mean, it helped that I stayed at SNL and kind of had stuff that I did there.

But like the older I got, I just didn't, you just stop caring what people think generally, you know what I mean? Like people are gonna think what they think. When you say it helped that you stayed at SNL, do you mean it helped you or it helped other people's perception of you? Maybe the other people's perception of me,

like that I worked with this different cast that came in and Will Ferrell and Tracy Morgan and that whole gang and did a non-Sandler achievement like that, some stuff. Yeah, cause I can certainly relate because having worked with Conan and I'm, and I actually was talking to Bobby Moynihan about this and saying, when you get older and you do something

that's like that everybody knows and it's your big thing and then you leave it and you think like, yeah, that was good, that was good. But oh, I got bigger fish to fry. And then you get older and you're like, nah, that was probably the biggest fish I'm gonna fry. You know? Okay.

Yeah, yeah, exactly. And then it's like, okay, fine. And then especially, I mean, and I'm sure you feel this when people let you know how much happiness, this, you know, the long hours and the silliness and the, you know, the work that has nothing to do with the work. You know, like all the time you spend fucking around that doesn't have anything to do with the work,

that how much, how happy it makes them. Yeah, and it's a good situation. Like Adam really, because he had started SNL as a writer, like he really esteems, and you know, that whole system of the writers produce their pieces and like he really is a very pro writer guy. And then I would go off and do some other stuff and they were like, thanks. And I'm like, don't you want to know what I think of, you want to run some cuts by me?

Like, no, we're good. Yeah. So it was like, I realized that I'm a good, I'm a writer for a guy who loves writers. Yeah. As a writer himself. Yeah. It's a tremendous situation. What's your favorite part of what you do?

I guess the validation of taking an idea and then seeing it kill in front of it. I used to say in a theater, but there's no more theater. So it's a test screening. So like just seeing, you know, it's still, which is the same thrill it was, you know, back in when San Luis doing standup, you know,up in the village, like seeing one of your jokes kill and seeing something that, with a movie you really have to, you know, SNL you

come up with that idea on Tuesday and it gets its up or down on on Saturday. But a movie you really fuck, it can take two years to shepherd a joke from an idea to a script to the shooting it, make sure the director doesn't fuck it up to make sure, can I swear? I'm sorry. Of course you can. You can fucking say whatever you fucking want. Oh, that shit.

Yeah, yeah. So, and then the editing process and right now we're sort of at the very final editing process of Happy Gilmore too. So there's jokes I came up with two years ago that I just have cherished and just making sure they make the final cut. And people laughing at them. It really feels like I earned it.

That's one of the hardest things is something you came up with that you think is funny and then hearing it 800 times and thinking like, no, it's still funny. Not just getting bored with it. Yes, that's a tremendous, you know, hazard of the occupation. Well, you better be done with that movie because it's coming out on July 25th.

What? Yeah. Happy Gilmore 2. And you've got Julie Bowen, Christopher McDonald, Ben Stiller all coming back. That's pretty great, you know. Is there, can you give a synopsis of what happens in this one and then really sell the shit out of it? No, it's the continuing adventures.

I've been such a jerk with everybody else about spoilers and calling Chris McDonald and saying, you can't say he goes on radio shows and I've been such a jerk about it, that I would be a jerk. Well, what happens, Andy, is what it's really about is. So there's no log line, it's all top secret? Yeah, I mean, there's, we went with-

You don't want the Chinese stealing Happy Gilmore too. Exactly, no, believe me, by the time the movie comes out, there'll be 50, it's, you know, We did go with sort of, and maybe not intentionally, with sort of some surprising stuff, and not just cameos, but like things. And a lot, some of it's leaked out, but some of it hasn't. So I don't wanna be the weak link in the chain. Is that a big worry when you're doing new stuff,

like leaking and, you know, and what do you do to combat it? You know, not usually, no. Yeah. Well, I mean, I hope this doesn't sound arrogant, but like a lot of times with our movies, we have to, you have to sell them. You have to get people interested in them.

Yeah. But this kind of, because it's a sequel, it has some built-in interests. So we feel like we don't have to do a big song and dance of like, oh, you're really, there's thrills, there's action. Yeah, yeah, yeah. It just kind of, it's, if you liked Happy Gilmore, here's some more.

Yeah. And so having to sell it less, why not preserve the surprise? You know, it's like cutting a trailer. Like we could definitely cut a much better trailer if we gave things away. Sure. And, but like, why do that to people?

Right, exactly. Yeah, let's save it up. Is there anything sort of like left undone? Like, do you have sort of... I mean, I, you know, I wanted to do Western and I did. And then I wanted to do a horror movie, which kind of was Huey Halloween. Yeah, yeah.

So I think, yeah, that's about it. I mean, I think I didn't know that I needed to do Happy Gilmore 2, we needed to do it, but like it's been a definitely a growth experience and cool and validation and kind of immersing ourselves in the love of that movie. We wrote it hoping that people would still remember it in 20 years, which was an insanely cocky thing to do.

And we just sort of have gone on with, you know, whatever the movie after movie after movie, and haven't really, you know, bathed ourselves in the fact that that movie had a life of, it's always on TV somewhere, and people, you know, wear happy Gilmore hats still, and like there's still some life to that movie, you know what I mean? And we haven't allowed ourselves to enjoy that too much.

What's the movie that people tell you the most about? Happy Gilmore. Happy, yeah, that's what I was gonna say. I would think, because you know, like the Wedding Singer is, you know, is quote unquote bigger than the other ones, but I would think Happy Gilmore is, cause that's just from my life.

That's the one that I hear people, you know, referencing and doing lines from and talking about, you know, so. Yeah, no, it's, you know, get the water boy some. Yeah, yeah, that's true. Yeah. Yeah, yeah, yeah. But definitely Happy Gilmore is number one. Yeah.

Nothing recent, I'll tell you that. Yeah. Or the, you know. From the 90s. Whatever, yeah. But definitely Happy Gilmore's number one. Yeah. Nothing recent, I'll tell you that. Yeah. Or the, from the 90s. Whatever, whatever. Little grownups. What are you doing next? Can you talk about what you're doing next? Or like you said, you're always kind of trying

to do the next thing while you're doing, before the one thing comes out, or is that no longer the plan? You know, Adam's already hard at work on some new stuff and I think I'm tangentially involved. He's not sure yet. No, he was CCing on me on all the emails and I was supposed to be reading this stuff

and I just didn't respond. So he stopped sending them to me. So I don't know if I'm still- You're my kind of student. I'm the same way. I emailed you about it like, oh yeah, I didn't read that. Sorry. No, if you ignore something, it'll go away.

So I was just like, he stopped CCing me on things. So I'm like, am I still producing that? I don't know. So you're not, yeah, you're just- I guess I'll do something in. Yeah, yeah. I'm gonna turn 60 in next year, 2026. Yeah, me too.

Yeah, that's right. 19 days after me. So yeah, so, you know, me too. Yeah, that's right. Yeah, yeah, yeah. 19 days after me. So yeah, so, you know, and I don't wanna overstay my welcome and my son's in the business now. So I, you know, trying to try and, you know, give him some advice, some bad advice.

Is he out here? No, no, he's at SNL. Oh, wow. Yeah, he's- Oh, that's right, I knew that. Yeah, so he's so, so seeing him go through some of the same things I did is fun and interesting.

But when your kid starts doing that, you start thinking, maybe I should leave the business and not be an old man doing the same things. No, no, you wanna top him at all times until you're in the grave. You wanna make him feel second to you. No, he has made his business to top me at everything. I was just kidding.

Oh, I know, it's really... Yeah. I was a writer at SNL. He's a writer who gets on. Yeah, yeah. I went to NYU. He went to NYU and graduated in three years. Wow.

I was a boy scout. He was an Eagle Scout. Like, he just... This kid just, you know... Shoving your face in the dirt every day. What did I ever do to him? Yeah. Besides love him and raise him.

Well, what do you think? Because, you know, you have had kind of a unique path through this. And I imagine you, you know, you know, like you're probably gonna have a nice summer. You know what I mean? You're gonna, I mean, I don't know. I, you got a lot going on in the summer or you get to kind of have some fun. You know, I had this idea that I was going to go away in August.

Yeah. It's going to go away for the whole month of August, but we got a dog, like an idiot. And I don't know what to do with the dog, man. Maybe give it away or something. Put a big pile of food in there. Would you wash my dog in? It's really a puppy. There's people that will do that for you.

I know, you can't trust them. Like your son, like give the dog to your son. That dog will be dead. Which, you know, would probably be a valuable lesson. Right, right, exactly. And then my dog problem is solved. Exactly. This might be a good idea.

But what do you think is the main thing that you've learned from your path through this? Main thing I've learned? Be roommates with Adam Zahler, I guess. The number one thing. That's when people would say, like, what, you know, like young people, like, what should I do to get into the business? I'd be like, well, first take improv classes, then become a sidekick on a late night talk show. Like, I don't know, just, you know. I mean, you do have to, I mean, I'm sure you had fun and you followed your fun to,

I mean, some people take this business very seriously and they have headshots and they're planning everything out and they're just going on audition after audition. But if you just sort of follow the fun, and some people, I knew accountants who loved being accountants, and lawyers who loved being, and that's great. And that's the way, there was a time when,

you sometimes had to choose between something that was steady, like being an accountant, and something like showbiz was just some weird thing that you probably weren't gonna be successful in. But why not give it a try? I used to like, people in my town used to send their kids to me when they wanted to be in show business.

I give them kind of a scared straight speech. Like, you know, you will probably be a waiter and watching your friends being. But I don't think that's true anymore. I don't feel like that in my mind. I feel like just do what you, if you wanna be an actor, you wanna be a comedy writer, do it.

And maybe be self-aware enough to know if you're no good at it. And if you're not successful, I'd say, hey, maybe I should try something, my second favorite thing to do or something. But yeah, I mean, I hate to be cliche, but yeah, follow your dreams. Yeah.

Well, now too, it's like for somebody of our age to give advice, like I've, you know, give it to talk to a class or something. And they'll be like, what should we do? I'm like, I don't fucking get on TikTok, I guess, you know, I mean, because it's a completely different thing. Yeah. I don't know how. I mean, if I was, if I was 20 and wanted to get into comedy now, I guess I would be like, well, get a TikTok account that you can do funny stuff on there. That's probably your quickest way to legit getting an agent

and all that other stuff. I know, yeah, that used to be the big thing, get an agent. And then if you want to be on SNL, like you go to either Second city or the groundlings. And then, you know, that was really how you got hired. Oh, maybe an occasional standup would break through. But I don't know how you get on Senate line. Well, Happy Gilmore 2 comes out July 25th.

I imagine this will be airing close to that. And it's been real thrill to have you. Thank you so much, Tim Harley. Hey, no, thanks for having me. Nice to finally meet you, Andy. And safe trips home. And I look forward to seeing the movie. engineered by Rich Garcia. Additional engineering support by Eduardo Perez and Joanna Samuel. Executive produced by Nick Leow, Adam Sacks,

and Jeff Ross. Talent booking by Paula Davis, Gina Battista, with assistance from Maddy Ogden. Research by Alyssa Grahl. Don't forget to rate and review and subscribe to The Three Questions with Andy Richter wherever you get your podcasts. And do you have a favorite question

you always like to ask people? Let us know in the review section. Can't you tell my love's a-growing? Can't you feel it ain't a-showing? Oh, you must be a-knowing. I've got a big, big love... This has been a Team Coco production.