Entertainment & Celebrity News Today | 2 Min News | The Daily News Now! - Sean Penn's 3rd Oscar: Joining Elite Club

Episode Date: March 16, 2026

Sean Penn wins third Oscar, joins elite club of actors with multiple wins. Support the show:Get a discount at https://solipillow.com/discount/dnn. Advertise on DNN:[e-mail] This is an automated, high-level news summary based on public reporting.Report issues to [e-mail]. View sources & latest updates:https://sources.thednn.ai/551da9db96d48a7a

Welcome to Entertainment and Celebrity News today. Two minutes of pop culture that matter. Sean Penn just snagged his third Oscar for Best Supporting Actor at the 98th Academy Awards. He won for playing the menacing Colonel Stephen Lockjaw in one battle after another, beating out a tough field including Delroi Lindo and Benicio Del, Toro. Penn first took home Best Actor for Mystic River in 2004, then again in 2009, for Milk. Before that, he earned nominations for Dead Man Walking, Sweeten Lowdown, and I Am Sam. This victory lands him in a rare group of actors, with three or more Oscar wins for performing.

Catherine Hepburn leads with four, while others include Ingrid Birdman, Merrill Streep, Jack Nicholson, Daniel DeLewis, Francis McDormand, and Walter. Brennan won three best supporting actor awards, including for The Westerner. Hepburn skipped ceremonies entirely, saying her real prize, was the work. Birdman spread her winds over decades, from gaslight to murder on the Orient Express. Penn kept up that Hepburn tradition by skipping the show, too. His lock-jaw role stands out as a chilling villain, and fans see of boosting his legendary status alongside these icons. A quick thank you to our sponsor of today's episode. Some travel miles to find peace. I just climb into bed and listen. S-O-L-I-SoliPillow.com.