40 Awkward Interviews That Made David Letterman A Legend For All The Wrong Reasons

Fans have picked up on Letterman’s tendency to sometimes ogle his female guests. Just look at his interview with Mariah Carey in 2001. He told her, “You look like a girl who likes to have fun.” But what makes this interview worse in hindsight is that Carey was having a rough year full of speculation about her mental health — Letterman touched on this as well — and it later turned out that she’d been diagnosed with bipolar disorder.

There was a point in the 2010s where Kathy Griffin seemingly got a taste for taking her clothes off. When she appeared on Letterman’s show in January 2012, he quizzed her about a previous strip in front of Anderson Cooper on New Year’s Eve. So what did Griffin do? She stripped-off again for him.

Charlize Theron went on Late Show in 2008 to discuss her new movie Hancock. But it seemed Letterman was more interested in talking about her body instead. He told her, “You look fantastic, beautiful, just gorgeous, a vision,” — fair enough on its own, but then the inappropriate jokes started. None of it would fly nowadays.

Chris Rock turned the tables on Letterman during a 2010 appearance on his show. Letterman was caught up in an infidelity scandal — and had a sore throat. Rock shot at him, “Things going bad, man? Wife still mad at ya, ain’t she?” Letterman managed to fight back with some jokes of his own, but the mic had definitely been dropped.

Cybill Shepherd’s dress actually arrived at the Letterman studio a week before her actual appearance in May 1986. So, never one to miss a gag, Letterman hung the dress up in the studio. What would Shepherd wear when she came on then? Well, she actually arrived in not a new dress but a towel. Yep, only the towel.

The X-Files star Gillian Anderson made her first Late Show appearance in February 1996. It was a mixed bag, to say the least. Anderson seemed pretty nervous, but Letterman asked some odd questions of her as well, including plenty involving aliens. The fact that Anderson being “easy” was mentioned also didn’t help matters.

Don’t recognize the name Rod Blagojevich? He was once the Governor of Illinois, and he appeared on Letterman’s show in 2009 specifically to tackle a bribery accusation. He didn’t end up doing himself any favors. His bizarrely upbeat behavior in the face of Letterman’s pointed questions made the show incredibly awkward to watch.

The 2011 Lady Gaga interview was odd to say the least. The singer wore an all-black outfit which Letterman compared to underwear, but then the questions about her actual career came. Letterman asked her if it was true she “once ate a Barbie doll’s head during a concert,” and Gaga proved it was just so by eating Letterman’s notes.

Kristen Stewart’s 2008 interview with Letterman went down in TV history for all the wrong reasons. The Twilight star was very nervous, the audience burst into laughter when she got a point about geography wrong, and Letterman seemingly didn’t really know what to do with her. But, believe it or not, she actually returned to the show a couple of years later.

In 2006 Howard Stern was waging a legal war with CBS. So when he appeared on the Late Show, which was on CBS, sparks flew. He showed up wearing a T-shirt with “I hate Leslie Moonves” printed on it — Leslie Moonves being the President of CBS. The network had to release a statement later saying that yep, they were still very much taking him to court.

Back in 2004 Janet Jackson suffered the embarrassment of having her breast exposed at the Super Bowl. So when she went on the Late Show that year, she was adamant she didn’t want to talk about it. Yet Letterman ignored her request and pushed her for info, showing very little respect for boundaries.

Some celebs like to flash Letterman. It makes for good TV, at least. Drew Barrymore did it in 1995 and then Courtney Love followed in 2004. Unfortunately, not long after leaving the taping of that show Love was arrested for unrelated reasons, and a downward spiral began. She next appeared on the show in 2010, and made her apologies.

Before anyone knew what a disaster the movie would be, Demi Moore went on the Late Show to promote Striptease in 1996. And she did it… As a stripper. She wore a skimpy outfit made out of index cards and proceeded to give Letterman a lap dance. Yep, it’s every bit as awkward as it sounds.

When Bill O’Reilly appeared on the Late Show in 2006, Letterman didn’t even bother to hide his dislike for the conservative commentator. The TV host snapped at one point, “You’re putting words in my mouth, just the way you put artificial facts in your head.” Believe it or not, Letterman once named O’Reilly as one of his favorite guests — for all the wrong reasons, though.

When Letterman’s past behavior was brought into question, a 2004 interview with Christina Aguilera was one of the ones unearthed. It makes for a very awkward watch today. For one thing he seems incredibly invested in what piercings she has, and for another he calls her “terribly exotic.”

In 2006 Letterman decided to pull a prank on fitness guru Richard Simmons. When Simmons appeared on the show he began demonstrating a food steamer, and as soon as he pressed the power button — boom. The steamer spewed out flames and Simmons just shrieked and ran. Letterman just laughed his head off as the cameras kept rolling.

When Uma Thurman went on the Late Show in 1995, Letterman pretty much just constantly flirted with her. He asked her if she would ever date a 48-year-old — that was his age at the time — called her “lovely” and specifically complimented her ears. It’s easy to forget she was actually promoting a movie, A Month by the Lake, because Letterman clearly wasn’t interested in that.

David Letterman never got along with eccentric comic-book writer and frequent guest Harvey Pekar. Eventually, Letterman outright vetoed anymore appearances from him after one particularly bad 1988 interview in which Pekar accused him of shilling for the General Electric company. Years later in 1995 Pekar told the Los Angeles Times newspaper, “Most people keep their mouth shut and let [Letterman] dump on them. I don’t wanna do that.”

Lauren Conrad’s 2008 appearance on the Late Show was always going to be somewhat awkward, because one of the reasons she went on was to dispel rumors of a sex tape. But Letterman upped the cringe factor by not only insulting The Hills star but mentioning he would’ve liked to see the tape.

Yes, everyone loves Dolly Parton. But David Letterman took things too far when she came on his show in 1987. He started off by complimenting her smell, and then as she was discussing Dollywood he suggested she marry him. Parton had been married for over 20 years at the time but she graciously said she’d “consider it.”

David Schwimmer must have wondered what he’d let himself in for when he went on the Late Show in 1996. That night the host had set up a “Letterman doll” in a chair which he would violently punch every now and again. When Schwimmer appeared, Letterman encouraged him to join in abusing the doll. It was extremely weird.

Gwen Stefani was another one who’s scent David Letterman commented favorably on. What’s the deal there? She had a lot to say on the show but Letterman couldn’t seem to help remarking on her body at any given opportunity. He told her at one point, “You have tremendous legs.” Hard to believe this interview happened as recently as 2005.

Justin Bieber was a love-him-or-hate-him performer back in 2012, and it was clear what side of this divide Letterman was on. When Bieber appeared on his show that year Letterman wore him down with constant uncomfortable jokes, plus he grabbed his arm and tried to rub his tattoo off at one point. That sort of thing can hurt.

Crispin Glover’s 1987 Late Night appearance went down in television history. When he appeared on the show he was dressed in a wacky wig, and then he started outright annoying Letterman with his erratic behavior. After he aimed a kick at Letterman’s face the host threw him out. Later on it transpired Glover was in character for a movie called Rubin and Ed, which wouldn’t be released until years later — but this appearance was terrible promotion for it.

Jessica Alba went on the Late Show to promote her film Honey in 2003. But Letterman was more interested in one particular aspect of the movie, namely her “tiny” dress. Despite her telling Letterman, “You’re making me nervous,” Letterman pressed on with “How tiny was it? Where was it tiny?”

Everything about director Harmony Korine’s Late Show appearance to promote Gummo in 1997 was incredibly awkward. The young filmmaker seemed very nervous, and Letterman was baffled as how to interview him. But many years later the host claimed he’d found Korine going through Meryl Streep’s things backstage and banned him from the show. Even more awkward.

David Letterman and Oprah Winfrey had a legitimate feud going at one point. Back in 1989 Oprah dealt with the topic of devil-worshiping on her show, and it did not go down well at all. The very next evening she appeared on Letterman’s show, and he didn’t stand up for her when the crowd began to heckle. A few nights after that Letterman made a crack about the food at Oprah’s restaurant, and she stopped speaking to him for over a decade.

Andy Kaufman’s 1982 appearance on Late Night with David Letterman was memorable to say the least. Attempting to promote himself as a wrestling champion, Kaufman fought Jerry Lawler with Letterman present and got knocked right off the stage. It was all staged and no-one was seriously hurt, but it was also super awkward.

Farrah Fawcett’s 1997 interview was just plain weird. She arrived late, for a start, and then began exhibiting behavior that just made no sense. She went off on tangents, drank Letterman’s coffee and was awestruck by the Manhattan backdrop in the studio. Many years later she claimed she was playing a character, if so, it was a very convincing one.

Letterman’s John McCain interview was awkward because… there was no John McCain interview. The politician was supposed to appear on the show in September 2008, but canceled at the very last minute. Letterman went on an extended rant about it in front of the cameras, especially when it transpired McCain had cancelled to do an interview with Katie Couric instead.

Madonna was, well, peak Madonna during her 1994 Late Show appearance. There were swear words, there were zingers, and there were inappropriate sexual comments from both sides of the desk. But Madonna later claimed that the writers of the show encouraged her to be unnecessarily provocative.

David Letterman thought he was getting Sacha Baron Cohen on his show for October 2006, but he got Borat instead. Letterman winced his way through the entire interview as Cohen’s most memorable character made some remarkably inappropriate remarks . It could’ve been a scene from one of the Borat movies.

After his time on the Late Show was up Letterman started a new show, My Next Guest Needs No Introduction in 2018. One of these guests was none other than Kim Kardashian, and her 2020 interview episode got pretty emotional. She was in literal tears at one point, and Letterman — a man who had mocked her in the past — had to comfort her.

Cher appeared on Late Night in May 1986 and immediately spoke her mind. When Letterman did his usual thing of telling guests they smelled nice she bit back with, “Is this as good as it gets?” And then, she outright told him some people thought he was “an a**hole.” Letterman began worrying about that… and unfortunately he probably had good reason to.

Joaquin Phoenix thoroughly upstaged David Letterman on one occasion. During one very memorable 2009 taping he appeared on the show looking unkempt, rambling, and claiming he was embarking on a new career as a hip-hop artist. It turned out to all be promotion for the 2010 film I’m Still Here… But Letterman wasn’t in on it.

Letterman’s 2013 interview with troubled star Lindsay Lohan is another one that got revisited years down the line. She came on the show to promote Scary Movie 5, but Letterman kept bringing up whether or not she was going to rehab and “what are they going to work on when you walk through the door?” And even though Lohan seemed uncomfortable, he kept on pressing.

Julia Roberts had something to say to Letterman when she appeared on his show in 2015. She’d almost turned down a previous appearance, she said, because she’d seen the host “absolutely dismember young actresses of my kind of peer group,” and feared she would be “left for dead and forgotten.” Though to his credit Letterman answered, “Well, I’m not going to dispute this.”

Jay-Z was interviewed by Letterman for My Next Guest Needs No Introduction in 2018. Right from the beginning there was an elephant in the room: the fact that both men had very publicly cheated on their wives. Their discussion of infidelity was never not going to be awkward, and it came off rather strained, but they did at least both take responsibility for their actions.

Even fans of Letterman and his mean sense of humor thought he was too harsh to Paris Hilton. She came on the show in 2007 to promote her new fragrance, but Letterman roasted her for having just got out of jail. She told him she didn’t want to discuss it, but he carried on regardless. He did actually apologize later, but later remarks from Hilton suggest that she never completely forgave him.

One incredibly uncomfortable Late Show scene drew outrage when it resurfaced later. The 1998 clip showed Letterman placing his hand on Aniston’s shoulder and then, without permission, sucking on her hair. Yes, really. The actress was shocked, and so are most people who see the clip today.