Jeremy Piven on Stand-Up, Entourage, and His Career-Defining Film 'The Performance'

On The Movie of Your Life with Richard Roeper, Jeremy Piven discusses pivoting from decades of acting into stand-up comedy, describing how he crafts an act with a set through line while staying open to improv, and previewing his June 12–14 run at the Chicago Improv in Schaumburg. He shares stories from growing up in Evanston with the Piven Theatre Workshop, his early influences, and how audiences sometimes confuse him with his Entourage character Ari Gold, including a backstage moment where Arch Manning said binging Entourage helped turn things around for him. Piven also dives into his passion project The Performance—based on an Arthur Miller New Yorker story—which took about 15 years to make and required him to train as a tap dancer, exploring themes of compromise and identity amid rising antisemitism. ----- 🎬 THE MOVIE OF YOUR LIFE with Richard Roeper Every one of us gets top billing in our own movie — but no great story happens alone. Join film critic Richard Roeper as he explores the connection between life and the movies we love. Featuring conversations with fascinating guests, deep dives into the best films of all time, and the question that drives it all: What's the movie of your life? 🎧 Listen & Subscribe: 🍎 Apple Podcasts → https://podcasts.apple.com/us/podcast... 💚 Spotify → https://open.spotify.com/show/26gN7OA... New episodes dropping regularly. Subscribe so you never miss one. 00:00 Arch Manning Inspired 00:58 Podcast Premise Intro 01:30 Meet Jeremy Piven 02:42 Why Stand Up Now 04:14 Crafting The Act 06:22 Evanston Roots Stories 09:53 Impressions And Special 10:59 Arthur Miller The Performance 13:50 Themes Tap And Timing 16:30 Chicago Community Grind 19:13 Indie Films Entourage Revival 21:05 Roeper Ari Gold Link 21:20 Roeper Rant Fallout 22:31 Siskel Origin Story 24:04 Sponsor Break 24:58 Apocalypse Now Awakening 26:45 Early Acting Influences 28:53 Romance and Obsession 33:17 Standup Audience Dialogue 34:45 Visiting Sling Blade Set 37:07 Never Retire as Artist 38:34 Limited Series Dreams 40:40 Farewell and Plug