20 years ago, Chris Stapleton left his small hometown in Kentucky and moved to Nashville to chase his dream of being a songwriter. Five years ago, the dream got bigger when he released his own album, won a pair of Grammy Awards, and established himself as one of the most distinctive voices in all of music. In this week’s “Sunday Sitdown,” Willie Geist gets together virtually with the country star to talk about that journey and his latest album, Starting Over.

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Matthew McConaughey is known for his free-spirited, easy-going philosophy on life, as embodied in his famous catchphrase “Alright, Alright, Alright.” The actor first uttered those words in the movie Dazed and Confused and they have followed him through a long career in Hollywood, from romantic comedies to TV series to an Academy Award for Dallas Buyers Club. In this week’s “Sunday Sitdown,” Willie Geist gets together with McConaughey over Zoom to talk about that journey, and what it was like to reflect on it in his new book “Greenlights.”

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Drew Barrymore has spent almost her entire life in the public eye, starting with her breakthrough role in E.T. at just 7 years old and continuing over four decades of acting, producing and directing. In this week’s “Sunday Sitdown,” Willie Geist gets together with the Hollywood star to talk about her long career in the spotlight and making the transition into daytime television with her new talk show “The Drew Barrymore Show.”

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45 years ago, a new era of American comedy began with the premiere of Saturday Night Live and a young producer named Lorne Michaels calling the shots. In this week’s “Sunday Sitdown,” Willie Geist gets together with the SNL creator and executive producer in famed Studio 8H to talk about the show’s legacy, and how they put on a live production in the middle of both a pandemic and a presidential election.

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Ina Garten has spent the last seven months of the pandemic at her home in East Hampton, trying out recipes for her new cookbook Modern Comfort Food with her husband Jeffrey as the lucky taste-tester. In this week’s “Sunday Sitdown,” Willie Geist gets together with the Barefoot Contessa for a virtual catch-up to talk about that new book and what it’s like to film her cooking show by herself at home. Plus Jeffrey and Willie’s wife Christina make a special appearance, as the couples get together for a cocktail party over Zoom.

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John Cusack has been on our screens for the better part of four decades, first in movies like Better Off Dead and Say Anything and later starring in classics like Grosse Pointe Blank and Being John Malkovich. In this week’s “Sunday Sitdown,” Willie Geist gets together with the actor over Zoom to talk about that long career of memorable roles and his latest shift into television with the new Amazon Prime series Utopia.

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DJ Khaled has made a name for himself in the music industry with his infectious beats and famous collaborators, but he’s also known for his relentless hustle, positivity, and self-confidence. In this week’s “Sunday Sitdown,” Willie Geist gets together with the radio DJ turned hip hop mogul to talk about his rise to the heights of music, his latest album, and what life has been like in quarantine with his wife and two young sons.

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Kelly Clarkson won the first season of American Idol nearly 18 years ago, and since then she has sold more than 45 million albums and won 3 Grammy Awards with her powerful voice. In this week’s “Sunday Sitdown,” Willie Geist gets together with the singer to talk about her transition into hosting a daytime talk show, her new music, and what life has been like during quarantine.

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The groundbreaking career of Mary J. Blige is all the more impressive when you consider she escaped a troubled childhood in the projects of Yonkers, New York and was discovered while doing karaoke at a local mall. In this week’s “Sunday Sitdown,” Willie Geist talks to the Grammy winner about her journey since then including her debut album “What’s the 411?,” the new music she’s been writing during quarantine and her latest venture into the world of wine.

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Chadwick Boseman passed away this week at the age of 43, losing a four year battle with colon cancer that he never discussed publicly. In this week's "Sunday Sitdown," Willie Geist revisits his interview with Boseman from 2018, when the actor soared to fame in the groundbreaking film Black Panther. They also discuss what it was like for Boseman to play some of history's most famous figures, including Jackie Robinson and James Brown. (Original broadcast date: March 4, 2018)

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