The Movie of Your Life with Richard Roeper

Richard Roeper talks with Henry Winkler about his prolific second career as a children’s author (42 books, including the upcoming “Detective Duck”), and how he “backed into” writing through his dyslexia. Winkler discusses his History Channel series “Hazardous History” (growing from eight episodes to 58), and career milestones from “Happy Days” and becoming The Fonz to “Night Shift,” “The Waterboy,” “Arrested Development,” and Emmy-winning work on “Barry.”

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Richard Roeper interviews Bob Odenkirk and David Cross about their documentary Bob and David Climb Machu Picchu, following their four-day, 26-mile Inca Trail trek that avoids gimmicks and captures honest moments, including reading letters from family. Cross explains wanting to see Machu Picchu and choosing Odenkirk as a companion, while both describe the main challenges as altitude and uneven ancient steps, their reliance on guides and porters, and reflections on doing big life goals before it’s too late.

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Richard Roeper discusses the larger-than-life legacy of Mike Ditka, including his impact on Chicago and his many on-screen appearances playing himself, then welcome actor Lyndsy Fonseca to talk about Hallmark’s "Holiday Touchdown: A Bears Love Story". Fonseca also reflects on keeping "How I Met Your Mother’s" ending secret and shares favorite films and holiday viewing.

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Richard Roeper welcomes director Patty Jenkins, discussing her unconventional path from camera work on music videos and commercials to leaving New York for AFI. Jenkins explains how Monster came together and reflects on the responsibility of making Wonder Woman.

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Richard Roeper interviews Lou Diamond Phillips about his 2026 crime thriller Gangland while Phillips describes his weary, nuanced tribal-cop character Teddy Sharp. He explains drawing on decades of playing law enforcement, time on reservations, being adopted into the Lakota and Cheyenne nations, and influences from his military-brat upbringing and father.

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Richard Roeper welcomes actor Dave Annable to discuss his career and his role as Dr. Neal McNamara on Taylor Sheridan’s Lioness, including how the show gained momentum and how Neil’s supportive-husband storyline flips traditional dynamics as the dangers of Joe’s work come closer to home in season three.

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Richard Roeper interviews actor Theo Rossi about his projects Come With Me (now in theaters and available on Apple TV), Bruton, and the breaking news that Rossi and several Sons of Anarchy castmates are reuniting for a new FX series, Legends, built around a clever, unexpected, Galaxy Quest/Curb-style premise.

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Richard Roeper interviews director-screenwriter Julia Hart about her Netflix hit Don’t Say Good Luck, which stars Sunny Sandler as a high schooler cast in Waitress while facing her mother’s cancer diagnosis, alongside Melanie Lynskey, Max Greenfield, Steve Buscemi, and Bebe Neuwirth; Hart explains how she, producer-husband Jordan Horowitz, and novelist Laura Henkin developed Henkin’s first screenplay and cast Sandler.

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Richard Roeper welcomes acclaimed comedian and actress Jane Lynch, discussing her tour with Kate Flannery (The Trouble With Angels), her Dolton upbringing, early jobs, and the moment at age 12 during a St. Jude “port of call” show that sparked her desire to perform.

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Richard Roeper interviews writer-director Michael Russell Gunn and actor Aya Cash about their film The Brink of War, set during the 1986 Reykjavik Summit where Reagan and Gorbachev’s private negotiations helped begin the end of the Cold War.

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The Movie of Your Life welcomes former MLB All-Star and two-time World Series champion Hunter Pence, who shares his love of baseball’s challenge, his transition into broadcasting, and advice for young players about pursuing what they love, embracing failure, and exploring roles beyond playing.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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