The Questlove Show - Questlove's Valentine's Day Music Picks - The Heartbreak Edition

Episode Date: February 13, 2026

As Valentine’s weekend arrives, Questlove follows his love-inspired soundtrack with a different kind of selection, one pulled from the side of the crate reserved for heartbreak. He suggests ten songs that sit with loss, loneliness, and love that’s run its course, spanning Jazz and Soul laments from Donald Byrd and Les McCann to more modern reflections by Mayer Hawthorne and Cleo Sol. Along the way, he shares the stories, anecdotes, and personal reflections that make these records ideal companions for a good cry — and, maybe, a little clarity. If this year finds you on the hurting or healing end of love, consider this episode your solace.See omnystudio.com/listener for privacy information.

This is an I-heart podcast. Guaranteed human. A win is a win. A win is a win. I don't care what you're saying. Yep, that's me. Clifford Taylor the 4th. You might have seen the skits,

my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw, unfills of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated.

So let's get to it. Listen to the Clifford show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok. This week on the Sports Slice podcast, it's all about the NFL draft. And we've got a special guest. The director of the NFL's East West Shrine Bowl, Eric Galco, joins the Sports Slice podcast to break down what really matters when evaluating draft prospects. From hidden traits teams look for to the biggest mistakes franchises make to the players flying under the radar. This is the insight you won't hear anywhere else. If you want to understand the draft

like an insider, you don't want to miss this episode. Listen to the Sports Slice Podcasts on the Iheart Radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Slice of Life 12 and TikTok podcast network on TikTok. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins. But the pregnancy appeared to be a hoax. You doctored this particular test twice, miscellins, correct? I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing.

Greg, a lesbian. Michael Mancini. My mind was blown. I'm Stephanie Young. This is Love Trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to Love Trapped podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands. I vowed, I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends, trust me, babe, on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.

A Questlove show is a production of I Heart Radio. Okay, you guys, as promised, I've shared my thoughts about 10 love songs that are perfect for any Valentine's mix. But I know on the other side of that coin, Valentine's could be a reminder of a love gone wrong. Love going wrong is a tragic in any person's life, but if anything, I can say that heartbreak and soul music, absolutely no strangers to each other. And that said, I would like to share some songs that I think if you want to sulk and kind of, you know, I'm very, familiar with the comfort of sadness. Sometimes feeling sad makes us feel good, which I don't recommend because that can lead to depression.

So, however, I'm a master of curation, so I will give you 10 songs that will kind of put you in the mood to cry if you feel like you need to do so. I'll say the number one song, probably the most mournful song that I know in jazz is Donald Bird's song called Christo. a Dentor. And oftentimes, this song gets chosen almost as a foreshadowing, like something bad's about to happen. I recall Spike Lee using this in the Malcolm X movie. First of all, it's mostly, it's a vocal choir, really doing the duties of the arrangements. There's a, you know, it's a jazz song with piano, upright bass, very light brush drums and chorus Donald Bird on the trumpet, but it's very mournful sounding, very sad sounding. I can't even lie to you. I can't even say that this is apropos for a funeral, I put a playlist together for my brother,

Michael Archer, DeAngelo. And this was my opening song. But even when I, I put a playlist together for my brother, But even when I put it on, like it brought the mood down and kind of the funeral director's like, do you have anything more celebratory? Like, you know, I know we're sad here, but, you know, I was like, yeah, okay, I went too far. So, but I will say that if crying is your goal, loneliness is your goal, you got to start with Christo Red Dentor by Donald Bird. It's on his album, a new perspective. Number two, long time QLS guests formerly known as Terrence Trindarby

now going by the name of Sonata Matreya. He has a song called Seasons. I'll be honest with you, Chris Rock put me on to this. He's like, yo, go to symphony or dam, which was his third album

after neither fish nor flesh. and I believe Symphony or Dam might have come out in 92, 93. There's a song called Seasons. And, you know, during that time period, I was going through a breakup. And the song actually kind of has a theory about the cycle of love, which is basically like sometimes you just love is a seasonal thing. Like, I know we are taught to think that, you know, this is the last person that you will be with.

You are stuck with this person for life, but sometimes love is seasonal. Sometimes, you know, depending on if you're a person that believes in astrology and the stars, like sometimes it's a 10-year thing. Sometimes it's a 20-year thing. Look, bands, the Beatles, love was a seven-year thing. The roots are in our 38th year of whatever. it is that we call this thing. But the song is actually executed very well. It's called Seasons.

And it deals with the realization of it. A relationship is over. And, hey, we had a good run, but love has seasons. All right. My third song in The Heartbreak Choice is by the one and only Don Blackman. Of course, holding you, loving you is a fan favorite, especially if you're Dillis Slim Village Head for samples. However, since you've been away so long,

is another song that's just as classic as holding you, loving you, less problematic, if you know what I mean, wink. Anyway, yeah, since you've been away so long, just talks about mourning of a relationship but it could also apply to just

not seeing someone for a long time you don't necessarily have to break up so like smart songwriters know not to add too much information Earthwin and Fire

was wise and very early to the game of taking pronouns out so that their song could apply to anyone sometimes as a songwriter if you present your lyrics or your course in a way that leaves the door open, you know, since

you've been away so long, could be about a breakup or could it just be about a long road trip and missing someone and I'm coming back? So the song applies to both, so I highly recommend it. My fourth song is a Stevie Wonder composition done with his first wife, Sarita Wright, former receptionist at Motown that he heard singing was like, hey, you should sing. And she's like, hey, I song write too. Sarita penned some of his greatest lyrics. I believe that in Stevie World, like, music is his main thing.

Like, lyrics are, I've seen and heard examples of him writing his songs. But, you know, he loves to collaborate with people. And Serita, I think, has written, like, just a lion's here, some of his greatest songs that we love. So her pin game is a match. And she has a song that she did on her second album called Stevie Wonder Presents Sarita. And it's called Because We Ended as Lovers.

Very sad song. It starts with rain. And she and Stevie also use the background choir kind of as a mournful kind of color that Donald Bird used. for Crystal Redentor. And because we ended as lovers is basically a plea to like, hey, even though we broke up, like let's not totally be out of each other's lives. I believe in amicable breakups.

If you break up with someone, I think you need a year off before you contact that person. And then you reenter their lives once the smoke is cleared. I think after a year you can be friends with your person. So also to know. note that Michael Simbello, if you're a fan of Flash Dance and you love the song, Maniac, many don't know that Michael Simbello was one of Stevie Wonder's greatest disciples. Like, he was in Wonderlove, his band for the longest, and co-wrote with Stevie a lot. So this is one of those songs as well that he's involved with.

I'll make it quasi-contemporary in bringing up Mayor Harthorne. not enough has been said about mayor's uh his production methods his tactics like he'll like he really nails the happy medium between something that's new and something that's classic and um i got to say that kind of mayors take on a delphonic's kind of slow jam and this song's called a strange arrangement which is the title track it's just a great gorgeous, gorgeous, gorgeous melody and arrangement. I love it so much that, yes, it's about a breakup. It's about someone that's realizing, oh, this is over.

He's like realizing it in real time that, oh, damn, I guess this is the end of the road for us. And so a strange arrangement by Mayor Hartthorne is number five. Number six, another unsung hero, Betty Davis. Betty Davis is an artist, singer, songwriter, producer. First black woman to produce her own music to get a credit for it, which, you know, her work that she released in the early 70s, women weren't really ever given agency to have their own ideas, and especially for black women.

And Betty's fight for her artistry is probably the thing that we know most about her. she also kind of did everything 10 years before anyone else so she was prince before prince and she was madonna before madonna she had entered miles davis life when she was just turning 1920 and um just her youthfulness and her her perspective on the world kind of had an effect on Miles Davis and this is why he created Bitches Brew. There is a song on a compilation called Is it Love or Desire?

And this song is just, it is called When Romance Says Goodbye. It's a very quiet song, very haunting, but also kind of wry and full of humor.

I love the way that she overannunciates the word love She calls it lavas. It's almost like five syllables. Lavas. Lavas. Betty Davis,

when romances, goodbye. Next up on the heartbreak list, of course, is a song called I'm Alone, an impromptu improv song by Bob McFerrin, now known as father of Taylor McFerrin and Javon and Javon McFerrin, of course, Madison McFerrin.

of course, Madison McFerran. But it's just a display of his mastery of handling multiple duties at once, as lead singer, as bass player, as multiple singers, just as a one-man show, and showing his humor as well. It's a song just talking about being alone, which sometimes isn't a bad thing. but he can't help but put humor in his music so this is one of those songs in which is kind of fun to hear the audience laughing at his punchlines because clearly he's making stuff up at the last minute so I'm alone by Bob McFerrin number eight very new if you know me

and you follow me on the socials you know that my love for the group salt is strong and the brightest star in that ensemble is, of course, Cleo's soul. And if you go to a Rose in the Dark album, there it is, man. You got to hear the song called I Love You, which could be misleading. Of course, I look at it and be like, oh, it's a love song. She's basically saying that I've heard everything coming out of your mouth except for the term, I love you. So this is a good example of how to communicate.

What needs aren't getting met in your relationship? So it's not necessarily a breakup. Oftentimes, relationships could go to dark emotional territory, and we often panic, because we don't know how to communicate with our significant other. And sometimes you need a song to help nudge you to say the words. So I would say that I love you by Cleo's soul, is that song. And that's at number eight. Number nine is a longtime favorite.

if you were a attendee or if you're on YouTube and you've seen a brothers in arms performance by me and my brother DiAngelo, I will say that we are, you know that we're very familiar and we know our way around an Ohio player song. And I will say that for this song, it is basically our love has died by the Ohio players. This is on their 1972 pleasure album, pleasure. And it's kind of, it's a rather defensive song because if you know the vocal stylings of Leroy, Sugarfoot, Varner, you know, kind of his baritone growl.

Ah, girl. Like, whenever it's time for the breakup song, especially if it's slow, it's time for Sugarfoot to come to the forefront. Of course, I want to be free as his most famous song, but if you listen to Our Love Has Died, I mean, the title in itself has pretty much tells you everything you need to know about the song. Yeah, our love is died by the Ohio players. And our final song in this sort of my top 10 go-toes for breakup songs

is it for heartbreak songs. Les McCann's has an album called Layers, and the title alone says it all. And it's called Sometimes I Cry. I highly recommend this. One of the biggest breakthroughs that I've had in therapy was sort of the shock look on my therapist's face when I was counting on two hands,

like the amount of times I've cried in a decade. and she's like, wait, you've only cried maybe 12 times in 10 years. And I was like, well, yeah, average, maybe one and a half times a year. You know, her jaw dropping on the floor. Look, it was how I was raised. I was taught we weren't supposed to cry. Now I cry at the drop of the hat because we're not going to survive. If we don't express our emotions, you don't want it to sit and down.

But sometimes I cry also. has a really gorgeous A-Bar Loop. And if you're a hip-hop head, I will say that Slickricks Behind Bars produced by Warren G. This is so weird that Warren G produced that song, and I will say that that song has like no trace of the G-funk that I'm accustomed to coming from Warren G. So when the Behind Bar song first came out, that remix,

the Warren G remix of it, of course I was expecting like, you know, some gangster. And it was far from that. It was, it almost felt like a triple quest produced it. Like, that's how weird it sounded to hear. Like, I kept checking like, wait, Warren G did this? So, but the sample, of course, comes from sometimes I cry by Les McCann. And so those are my 10 heartbreak songs. don't don't get too comfortable in heartbreak like it's it's good to get your emotions out but

don't live there all right well that's my take on valentine songs you should check out peace a win a win a win a win i don't care what i'm saying yep that's me cliford taylor the fourth you might have seen the skits my basketball and college football journey or my career in sports media well now i'm bringing all of that excitement to my brand new podcast the clifers show This is a place for raw, unfilled of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to The Clifford Show on the IHeard Radio app, Apple Podcast, or wherever you get your podcast.

And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok. This week on the Sports Slice podcast, it's all about the NFL draft. And we've got a special guest. The director of the NFL's East West Shrine Bowl, Eric Galko, joins the Sports Slice podcast to break what really matters when evaluating draft prospects, from hidden traits teams look for, to the biggest mistakes franchises make, to the players flying under the radar.

This is the insight you won't hear anywhere else. If you want to understand the draft like an insider, you don't want to miss this episode. Listen to the Sports Slice podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Slica Life 12 and TikTok Podcast Network on TikTok. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins.

But the pregnancy appeared to be a hoax. You doctored this particular test twice, Ms. Owens, correct? I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing. Greg, a lesbian, Michael Marincini. My mind was blown. I'm Stephanie Young.

This is love trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to a love-trapped podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands. I vowed, I will be his last target. He is not going to get away with this.

He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends. Trust me, babe, on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. This is an IHeart podcast. Guaranteed human.