The Movie of Your Life with Richard Roeper

Wayfarer Theaters

Now think about it. Every one of us gets top billing in our own movie, but no great story happens alone. Life comes with an ensemble cast. On this show, we're gonna explore that connection between life and the movies we love. Now, often I'll be joined by people who have amazing stories and we'll talk about the films that shaped who they are.

Other times we're gonna go on deep dive, maybe the best movies for the holidays, unforgettable performances too. Paying tribute to the great actors of our time. We also wanna hear from you. What's the movie of your life? The one film that you'd watch again, if you could only watch one movie one last time.

It's the Movie of Your Life podcast.

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21 episodes
Updated Friday

Episodes21

Newest first

Friday · 30 min
Hollywood's Big Summer: Spider-Man, The Odyssey, and the Movies Everyone's Talking About
Richard Roeper reflects on an historic 2026 summer at the movies and the recurring claim that “movies are dead,” tracing past disruptions from TV and VHS to streaming and the pandemic’s theater closures, including Chicago’s Navy Pier IMAX. They discuss major hits led by Spider-Man: Brand New Day—praised for its grounded, emotional story about Peter Parker being erased from everyone’s memory—and Christopher Nolan’s The Odyssey, a true-IMAX epic projected to top $1.5 billion despite “woke casting” backlash. Roeper shares highlights from his private New York screening and extensive interview with Nolan, including Nolan’s admiration for Orson Welles and Citizen Kane, plus Roeper’s history with Nolan since Memento and The Dark Knight. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 31 · 36 min
Laura Benanti
Tony Award-winner Laura Benanti discusses her autobiographical one-woman comedy show, "Laura Benanti: Nobody Cares", coming to Chicago for five performances at Steppenwolf’s downstairs theater, and why playing herself in a show she wrote feels more vulnerable than performing someone else’s material. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 23 · 30 min
Holly Brown
Richard Roeper interviews stand-up comedian and podcaster Holly Brown about her dark comedy podcast "Everybody Knows But Me", inspired by her father’s deathbed confession that he had twin sons everyone else in the family knew about. Brown, a Valley girl raised in Los Angeles whose dad worked on ’90s sitcoms including Frasier, explains how she uses sitcom structure, actors, and sound design to process grief, family dysfunction, and healing through humor, and teases whether she eventually meets her half-brothers. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 14 · 28 min
Steve Sarowitz
Richard Roeper interviews Steve Sarowitz, Paylocity founder and chairman/financial backer of Wayfarer Studios and Wayfarer Theaters. Sarowitz addresses recent legal controversy involving Justin Baldoni, saying accusations were false and his Baha’i faith and loyalty to Baldoni helped him endure the ordeal. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 2 · 29 min
Beth Lane
Richard Roeper talks with filmmaker and actor Beth Lane about her Netflix documentary Unbroken, which chronicles the true story of seven Jewish siblings hidden for two years outside Berlin during World War II, the only known family of seven to survive the Holocaust together before being separated in foster care after arriving in America. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 25 · 34 min
Gary Cole
Actor Gary Cole discusses returning to the Chicago stage for the first time in 25 years to star in Mia Chung’s Catch as Catch Can at Steppenwolf Theatre during its 50th anniversary season (running through July 12). Cole also shares favorite films, his first impactful theater movie, a surprising in-room Entourage casting, and his choice of a dream set to observe. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 18 · 37 min
Ketch Secor & David Greene
Richard Roeper welcomes journalist-filmmaker David Greene and Old Crow Medicine Show’s Ketch Secor to discuss their documentary Louder Than Guns, created after the Covenant School tragedy in Nashville to explore whether music, conversation, and community can help bridge America’s gun divides. Join Greene and filmmaker Doug Pray June 24th at Wayfarer Theaters Highland Park for a screening of the film and Q&A. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 11 · 29 min
Corey Hendrix
Richard Roeper welcomes Corey Hendrix, a West Side Chicago actor known for The Chi, Fargo, and The Bear, discussing how Chicago’s theater and improv communities shaped his craft and his commitment to authenticity in Chicago-set stories. He shares advice for aspiring actors, details preparing for Sweeps’ sommelier arc in The Bear through tastings and experts, and names the films that were influential to him. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 5 · 43 min
Jeremy Piven
Actor and longtime comic Jeremy Piven, known for his Emmy and Golden Globe-winning work as Ari Gold on Entourage, discusses his storied film and television career. Piven is currently on the road and Chicago area folks can see his stand-up June 12–14 at the Chicago Improv in Schaumburg. Tickets at improv.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 8 · 24 min
Filmmaker Olivia Newman & author Shelby Van Pelt
Richard Roeper hosts Olivia Newman and Shelby Van Pelt to discuss the Netflix film adaptation of Van Pelt’s "Remarkably Bright Creatures", starring Sally Field. Newman describes the key adaptation challenges and casting Alfred Molina as Marcellus’s voice. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 1 · 27 min
Denise Richards
Denise Richards stars in the indie thriller "Dirty Hands" now available on Apple TV and Prime Video. Richards discusses how promoting the film has changed following the sudden death of actor and co-star Patrick Muldoon and also reflects on her Seinfeld “The Shoes” guest spot, her 1990s run (Starship Troopers, Wild Things, The World Is Not Enough, Drop Dead Gorgeous), her interest in comedy, and her moviegoing memories. Learn more about your ad choices. Visit megaphone.fm/adchoices
April 24 · 36 min
Brian Koppelman
Writer-director and Billions co-creator Brian Koppelman discusses his career, creative habits, and films that influenced him. Koppelman describes building “scaffolding” through morning pages, transcendental meditation, and journaling to overcome creative blocks. Learn more about your ad choices. Visit megaphone.fm/adchoices
April 9 · 30 min
Top Picks of Inspirational Sci-Fi Flicks
Richard Roeper compares reactions to Project Hail Mary and other space/alien films with an inspirational tone: from Close Encounters of the Third Kind to Interstellar, touching on themes of benevolent aliens, survival, and what comes after a mission. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 25 · 25 min
Kendall Gill: March Madness and his surprising favorite movies
Richard Roeper welcomes Chicago native and 15-year NBA veteran Kendall Gill (University of Illinois “Flyin’ Illini,” fifth overall pick in the 1990 NBA Draft, former steals leader, now a Bulls analyst). Gill previews Illinois’ Sweet 16 matchup with Houston, saying Thursday’s game is the key to a potential Final Four run and don't miss his surprising guilty pleasure movie pick. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 20 · 33 min
Spacewoman: Col. Eileen Collins on risk, family, and the Space Shuttle program
Richard Roeper welcomes pioneering astronaut Colonel Eileen Collins to discuss the documentary Spacewoman, directed by Hannah Berryman, and Collins’ appearances at Wayfarer Theaters in Highland Park on March 30. Collins reflects on being the first woman to pilot and command a space shuttle, the personal costs of sharing family history in the film, and why the shuttle program ended in 2011 in favor of safer capsule designs with escape systems. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 13 · 41 min
Oscar Predictions
Recorded live at a Wayfarer Theaters event, Richard Roeper reflects on covering the Oscars, including intense security, red-carpet realities, and why hosting is a thankless job, citing favorites like Billy Crystal and Steve Martin. Roeper also run through major-category predictions, highlighting films including One Battle After Another, Sinners, Hamnet, Song Sung Blue, Weapons, Train Dreams, and Marty Supreme. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 4 · 21 min
Piper Curda
Richard Roeper talks with Piper Curda about voicing Mabel in Disney Pixar’s "Hoppers" and the challenges of recording animation alone while creating physical, action-heavy performances in the booth. They also discuss themes of family and community, plus Piper’s most formative and favorite movies. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 2 · 36 min
Amy Landecker and Bradley Whitford
Richard Roeper welcomes filmmakers and actors Amy Landecker and Bradley Whitford to discuss their new film "For Worse", which Landecker wrote and directed and Whitford co-stars in and produces, drawing inspiration from Landecker’s post-divorce wedding experience, an age-gap acting-class connection, and romcom wedding-movie traditions. Learn more about your ad choices. Visit megaphone.fm/adchoices
February 24 · 32 min
Oscar-Winning Director Morgan Neville
The Oscar, Grammy and Emmy-winning directors talks about his new film, "Paul McCartney: Man on the Run," which covers McCartney’s post-Beatles reinvention with Linda, the formation of Wings, public misconceptions around the breakup, and Neville’s archival, journalism-driven approach. "Man on the Run" premieres on Prime Video on Feb. 27th. Learn more about your ad choices. Visit megaphone.fm/adchoices
February 20 · 34 min
Remembering Robert Duvall
Richard Roeper celebrates the late Robert Duvall, sharing personal memories (including Roeper’s day on the Widows set) and revisiting key performances across his career such as The Godfather films, Open Range, Lonesome Dove, and his self-made passion project The Apostle. Learn more about your ad choices. Visit megaphone.fm/adchoices