With that in mind, we give you this roundup of some of the most memorable late-night interviews of the past 40 years. (We’re focusing mainly on the post-Johnny Carson era, so none of the legend’s interviews are included here.)
Cher on ‘Late Night With David Letterman’ (May 22, 1986)
After repeatedly declining invitations to “Late Night With David Letterman,” Cher pointedly confessed she didn’t think much of the host’s interviewing style in her first appearance on the NBC show, calling him an “a — hole.” The pair went on to have a number of playful exchanges over the years before Letterman’s 2015 retirement.
Ahead of his final “Late Show” bow, Cher paid Letterman a surprise visit. “For a number of years, there’s something that I’ve always wanted to get straight between us,” she told him. “This is one thing that I really mean from the bottom of my heart — I’m not kidding. … I really love you, and I’m going to miss you.”
Magic Johnson on ‘The Arsenio Hall Show’ (Nov. 8, 1991)
Just one day after telling the world he was retiring from the NBA, after being diagnosed as HIV-positive, Earvin “Magic” Johnson appeared on Arsenio Hall’s show. A smiling Johnson, who was welcomed with a standing ovation, spoke frankly about his diagnosis and urged viewers to practice safe sex and educate themselves about the virus that causes AIDS.
Reflecting on the historic moment decades later, Johnson told “Access Hollywood” that, at the time, he wanted to do only one talk show — the one hosted by his good friend Hall. “He’s been with me through all my highs — all the championships, when I won. He would cry with me when we lost,” Johnson said. “And then this moment was another moment that I wanted to share with the world, but I needed a friend and a support system.”
Bill Clinton on ‘Arsenio’ (June 3, 1992)
Bill Clinton’s 1992 appearance on “The Arsenio Hall Show” began with the presumptive Democratic nominee playing “Heartbreak Hotel” on the saxophone, yielding more than one headline about the then-governor of Arkansas tooting his own horn. But the appearance, which also included an interview with the late-night host, was an iconic moment for Clinton’s campaign and public image.
“I’ve got to convince them that I am not just another politician, that I passionately believe what I am saying and that I’m tough enough to do it, that I am determined enough to do it,” he told the Associated Press ahead of his appearance on Hall’s show.
Madonna on Letterman’s ‘Late Show’ (March 31, 1994)
Madonna’s 1994 appearance on CBS’s “Late Show” is the most obvious entry on this list. Madonna used the f-word 14 times during the interview, in which she repeatedly insulted Letterman and resorted to clumsy innuendo. (“That microphone is really long.”) “You realize this is being broadcast, don’t you?” Letterman asked at one point.
The singer also made a crass complaint to Letterman’s audience: “I gave him a pair of my underpants and he won’t smell them.” And as former “Late Show” producer Daniel Kellison recalled in a piece for Grantland, Madonna lingered well after the bizarre interview’s intended end, forcing producers to bump the episode’s other guests.
The controversial interview led to FCC complaints, a searing Entertainment Weekly column that essentially pronounced Madonna’s career kaput and — as the same column noted — some of the highest ratings Letterman had seen since his 1993 debut on the network. The two alluded to the interview months later at the MTV Video Music Awards.
“And you thought we wouldn’t last,” Madonna quipped.
“I’ll be in the car,” Letterman deadpanned. “Watch your language.”
Madonna later told Spin that the show’s producers had encouraged her to curse. The singer, citing violence on TV, called the outcry over her use of the f-word “ridiculous” and “hypocrisy.” She also took issue with the show’s decidedly sexist intro, which Kellison conceded “probably didn’t help matters”: “Our first guest tonight is one of the biggest stars in the world, and in the past 10 years she has sold over 80 million albums, starred in countless films and slept with some of the biggest names in the entertainment industry.”
Drew Barrymore on ‘Letterman’ (April 12, 1995)
By the time Drew Barrymore was 8 years old, she had already hosted “Saturday Night Live” and appeared (multiple times) on Johnny Carson’s “Tonight Show,” so the actress was no stranger to the after-hours circuit when, at 20, she appeared on “Late Show” in 1995. But she managed to surprise the legendary host — who happened to be celebrating his 48th birthday — by hopping onto his desk and flashing her breasts.
Barrymore reflected on the infamous moment during a 2018 interview with Stephen Colbert, whose CBS show tapes in Letterman’s old theater. “It’s like a distant memory that doesn’t seem like me,” the actress said. “But it is me. And that’s kind of cool. I’m still down with that.”
Norm Macdonald and Courtney Thorne-Smith on ‘Late Night With Conan O’Brien’ (May 15, 1997)
When Norm Macdonald, then-host of SNL’s “Weekend Update,” visited Conan O’Brien’s “Late Night” in 1997, he greeted the host with a graphic description of his recent illness.
The show went predictably off the rails after that, but this episode is perhaps most memorable for Macdonald’s uninhibited reactions to O’Brien’s questions about fellow guest Courtney Thorne-Smith’s “Chairman of the Board” co-star Carrot Top: “Wait a minute, she left ‘Melrose Place’ to do a movie with Carrot Top?” And: “If Carrot Top’s in it, you know what a good name for it would be? ‘Box Office Poison.’ ”
After much teasing, O’Brien taunted Macdonald when Thorne-Smith revealed the name of the movie, saying, “Do something with that, you freak.” Macdonald retorted, “I bet the ‘board’ is spelled B-O-R-E-D.”
Harmony Korine on ‘Letterman’ (Aug. 10, 1995)
Following his ’90s breakout “Kids,” screenwriter Harmony Korine made a series of “Late Show” appearances so legendary that the A.V. Club once proclaimed them the filmmaker’s best work. Korine first appeared on the show in 1995 to promote the controversial Larry Clark-directed film, but he frequently veered into elaborate rambling. For example:
“Once I took this kid sailing — his name was Barfunk — and I capsized the sailboat,” Korine told Letterman during his first appearance. “And he almost drowned.” (“Wow,” the host replied.)
Korine made his final “Late Show” appearance in 1998, greeting Letterman in a gray hoodie, yellow T-shirt and baggy jeans. “Thanks for fixing yourself up for this,” Letterman said. “Skateboard park closed?” In 2013, when James Franco visited the “Late Show” to promote Korine’s “Spring Breakers,” Letterman revealed that he banned Korine from the show after catching him going through Meryl Streep’s purse backstage.
Kanye West on ‘The Jay Leno Show’ (Sept. 14, 2009)
One day after crashing Taylor Swift’s big moment at the 2009 MTV Video Music Awards, Kanye West appeared on “Jay Leno” to explain his widely criticized stunt. “It was rude, period,” West said, noting that he wanted to apologize to the singer in person. The interview took an awkward turn after Leno asked the rapper what his mother, Donda, who died in 2007, would have thought about the incident. The rapper, who was very close to his mother, appeared to stifle tears as he paused for several seconds.
“Would she be disappointed by this? Would she give you a lecture?” Leno pressed.
“Obviously, I deal with hurt, and so many celebrities, they never take the time off. And I’ve never taken the time off,” the rapper responded. “I’m just ashamed that my hurt caused someone else’s hurt.”
The rapper added that he planned to take a hiatus “to analyze how I’m going to make it through the rest of this life, how I’m going to improve.” Though West has never quite lived down his award-show antics, he may have earned some sympathy due to Leno’s extremely personal question.
Hugh Grant on 'The Tonight Show With Jay Leno’ (July 10, 1995)
When Hugh Grant was arrested and charged with misdemeanor lewd conduct with a prostitute in late June 1995, he was just weeks away from a scheduled appearance on Leno’s “Tonight Show” to promote his upcoming film “Nine Months.” And as The Washington Post and other news outlets reported the next day, he was still expected to appear on the late-night show despite the scandal.
Grant was praised for his honest response to Leno’s first question, “What the hell were you thinking?”: “I think you know in life pretty much what’s a good thing to do and what’s a bad thing, and I did a bad thing,” the actor said. “And there you have it.”I see you do every night,” Stewart told the “Mad Money” host.c
Joaquin Phoenix on ‘Letterman’ (Feb. 11, 2009)
Joaquin Phoenix has become known for his late-night antics, but in 2009 it just seemed baffling when the actor turned up on “Late Show” looking like a “Blues Brothers” extra in his dark suit and sunglasses. He also spoke very little — despite Letterman’s many attempts to engage him on his role in the romance drama “Two Lovers” and his announcement, months earlier, that he planned to retire from acting and pursue a career in rap. The host filled the awkward silence with cracks about Phoenix’s new look: “What can you tell us about your time with the Unabomber?”
When Phoenix returned to “Late Show” a year later, he confirmed suspicions that his strange behavior had been a joke. The actor explained that, unbeknown to Letterman, he had been playing the character at the center of the 2010 mockumentary “I’m Still Here.” The actor apologized, telling Letterman that he and collaborator Casey Affleck (then Phoenix’s brother-in law) “wanted to do a film that explored celebrity between the media and the consumers and the celebrities themselves.”
Jim Cramer on ‘The Daily Show With Jon Stewart’ (March 12, 2009)
After a week of criticizing CNBC’s coverage in the lead-up to the 2008 financial crisis, Jon Stewart finally welcomed the network’s Jim Cramer onto “The Daily Show,” where the Comedy Central host unleashed scathing criticism of what he saw as the business news network’s failure to anticipate the crisis. “I can’t reconcile the brilliance and knowledge that you have of the intricacies of the market with the crazy bullsh-- I see you do every night,” Stewart told the “Mad Money” host.
Many media outlets crowned Stewart the winner of the showdown. For his part, Cramer cast the moment as a low point in a 2011 New York Times Magazine profile. He also confessed that he hadn’t been ready for what awaited him in the “Daily Show” studio.
“It’s unbelievable, I know, but I never saw it coming,” he told the magazine. “The night before Stewart, a bartender in Brooklyn wished me luck, and I didn’t get what he was talking about. I expected a cordial discussion.”
Maurice Sendak on ‘The Colbert Report’ (Jan. 24, 2012)
In some ways, Colbert’s lively 2012 chat with Maurice Sendak, the beloved author and illustrator of “Where the Wild Things Are,” foreshadowed the authenticity that the host would later bring to “The Late Show.” Sendak — who appeared on “The Colbert Report” just months before his death at 83 — memorably told Colbert: “I don’t write children’s books. I write, and somebody says, ‘That’s for children.’ ”
Donald Trump on ‘The Tonight Show Starring Jimmy Fallon’ (Sept. 15, 2016)
Fallon’s famously apolitical approach to late night backfired when the “Tonight Show” host playfully tousled Trump’s hair just months before the 2016 election. Fallon’s critics derided the playful interview as “normalizing” the presidential nominee, while Fallon’s contemporaries called Trump out for his divisive rhetoric.
Kellyanne Conway on ‘Late Night With Seth Meyers’ (Jan. 10, 2017)
When senior Trump adviser Kellyanne Conway appeared on “Late Night” in 2017, the timing couldn’t have been better. Just hours earlier, CNN reported that Trump had been briefed by intelligence officials on allegations that Russia had obtained compromising information about the president-elect. Meyers was ready, calling Conway out for pivoting away from tough questions and grilling her on the president’s response to that evening’s breaking news.
The “Late Night” host later told GQ that his show’s live audience gave him the advantage over his cable news counterparts. “There was a moment where I said to Kellyanne, ‘That’s a pivot,’ ” Meyers recalled. “I feel like if Jake Tapper said that, she’d say, ‘No, it’s not,’ and explain why it wasn’t a pivot. But when I said, ‘That’s a pivot,’ the audience laughed, and it took away her ability to lie. She would not just be saying that I was wrong but 200 other people were wrong.”
Joe Biden on ‘The Late Show With Stephen Colbert’ (Sept. 10, 2015)
After a bumpy start as Letterman’s successor, critics (and viewers) watched as Colbert found his footing in the politically charged aftermath of Trump’s election. But as the host told his friend and collaborator Stewart several years ago, it was his 2015 conversation with Vice President Joe Biden that really helped Colbert define his presence on the late-night show.
Colbert was widely praised for the emotional interview with Biden, who appeared on the show just months after the death of his eldest son, Beau. Colbert and Biden connected on two things they have both discussed publicly throughout their respective careers: grief and their Catholic faith. As a young senator, Biden lost his wife and infant daughter in a car accident; Colbert was 10 years old when two of his brothers and his father died in a plane crash.
“Only I, my real self, could have received what Mr. Biden was willing to share with me and with the audience,” Colbert told Stewart.
An earlier version of this story incorrectly stated that Stephen Colbert tapes in Johnny Carson's old theater. Like his predecessor, David Letterman, Colbert tapes in the Ed Sullivan Theater. Additionally, Kanye West's interview with Jay Leno did not take place on Leno's "Tonight Show"; the interaction was on the inaugural episode of "The Jay Leno Show." This version has been corrected.