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The Most Uncomfortable Letterman Interviews Ever

In many regards, David Letterman is the perfect antidote to the airless celebrity interview. During his long, legendary tenure as a late-night talk show host, he earned a reputation for keeping guests on their toes, occasionally insulting visitors, taking pleasure in puncturing their pretenses, and cracking plenty of jokes at their expense. Letterman even admitted as much during a Justin Bieber interview in 2012: "That's what I do," he laughed. "I make people feel uncomfortable."

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The Most Uncomfortable Letterman Interviews Ever

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    The Most Uncomfortable Letterman Interviews Ever

    The Most Uncomfortable Letterman Interviews Ever

    In many regards, David Letterman is the perfect antidote to the airless celebrity interview. During his long, legendary tenure as a late-night talk show host, he earned a reputation for keeping guests on their toes, occasionally insulting visitors, taking pleasure in puncturing their pretenses, and cracking plenty of jokes at their expense. Letterman even admitted as much during a Justin Bieber interview in 2012: "That's what I do," he laughed. "I make people feel uncomfortable."

    David Letterman's Most Controversial Moments

    David Letterman's Most Controversial Moments

    David Letterman has taped his final episode of the 'Late Show,' ending a successful, indelible 33-year run on late-night television. As with many long careers in show business, Letterman's was filled with as many highs as lows. In fact, the Ed Sullivan Theater, which hosted the 'Late Show' for decades, was often the setting for some of the most talked about and controversial television moments in modern-day history. We've pulled together nine times the 'Late Show' truly made our jaws drop. Check them out, below.

    Dark Secrets Of Late Night Talk Show Hosts

    Dark Secrets Of Late Night Talk Show Hosts

    Late night is a very specific and rarified perch of TV. While a network may offer dozens of shows in its primetime lineup, only one person (almost always a man) gets to host its late-night show for five nights a week. It's a job a lucky entertainer will hold onto for years, virtually tucking in millions each night with their topical monologue jokes, softball celebrity interviews, and maybe a party game or a comedy sketch.

    Talk Show Hosts Reveal Their Worst Guests Ever

    Talk Show Hosts Reveal Their Worst Guests Ever

    While everyone loves a really compelling interview, talk shows — much like everything in pop culture — thrive on drama. Throughout talk show history, some of the most memorable moments were also the most confrontational, including David Letterman's awkward talk with Joaquin Phoenix or Arsenio Hall standing his ground against protestors.

    The Truth About Regis Philbin And David Letterman's Relationship

    The Truth About Regis Philbin And David Letterman's Relationship

    Legendary talk show host Regis Philbin passed away on July 24, 2020. The next day, his family revealed the sad news with a statement to People, sharing, "We are deeply saddened to share that our beloved Regis Philbin passed away last night of natural causes, one month shy of his 89th birthday." The statement continued, "His family and friends are forever grateful for the time we got to spend with him – for his warmth, his legendary sense of humor, and his singular ability to make every day into something worth talking about. We thank his fans and admirers for their incredible support over his 60-year career and ask for privacy as we mourn his loss."

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