From Rocky to Rambo to his latest hit Tulsa King, Sylvester Stallone has spent decades defying the odds. Long before Hollywood stardom, he was a struggling actor in a New York apartment, writing the script for Rocky that would change his life. In this Sitdown, Stallone reflects on the hardships that fueled his drive, why he refused to let anyone else play Rocky, and how receiving the Kennedy Center Honors has impacted his perspective on legacy.

Grammy Award-winning artist Bad Bunny sat down with Willie Geist to discuss his historic concert residency in Puerto Rico and his foray into acting with his latest movie "Caught Stealing".

Alicia Keys is a musical powerhouse, known for her timeless voice, soulful ballads and fearless artistry. In this conversation from April 2024, she joins Willie ahead of the Broadway debut of Hell’s Kitchen, the coming-of-age musical inspired by her life. Alicia reflects on the decade of work it took to bring the show to the stage, the personal stories behind it, and the enduring legacy of her music.

Machine Gun Kelly has built a career on defying expectations, first breaking out as a Cleveland rapper, then reinventing himself as a punk rock star. In this chat from October 2021, MGK opens up to Willie about his musical evolution, his high-profile relationship with Megan Fox, and how music has carried him through fame, anxiety, substance abuse, and loss.

Olivia Rodrigo skyrocketed to global fame with her record-breaking debut Sour, reshaping pop music with her voice, lyrics, and honesty. In this conversation from September 2023, she and Willie talk about the release of her sophomore album Guts, the way she tells stories through her music, and why she refuses to reveal the true inspiration behind her hit single “Vampire.”

Few artists have walked a path like Jelly Roll, who grew up surrounded by struggle and addiction before choosing redemption. In this sitdown from October 2024, Jelly Roll talks with Willie about his transformation from rapper to country star, the resilience that shaped his music, and the persistence that led him to selling out arenas across the country.

Known for his quick wit, Vince Vaughn has been a fixture of Hollywood comedies for more than two decades, starring in hits like Swingers and Wedding Crashers. In this Sunday Sitdown from May 2025, Vince joins Willie Geist at Enoteca Maria on Staten Island, the Italian restaurant that inspired his new Netflix film Nonnas. They talk about his career of iconic roles and even meet Joe Scaravella, the man who's life inspired the story of the film.

Maya Rudolph knew early on she was born to make people laugh, but her run on Saturday Night Live cemented her place as a comedy powerhouse. In this chat from September 2018, Willie sits down with Maya inside SNL’s iconic Studio 8H to talk about her favorite celebrity impressions, working alongside icons like Tina Fey and Amy Poehler, and how the show became her comedy boot camp, paving the way for hit roles in Bridesmaids and her Amazon series Forever with Fred Armisen.