David Letterman was a mainstay of the talk show circuit for over 30 years. The Late Show With David Letterman pulled in high ratings for CBS and played host to the biggest names in showbiz. But he now faces the very real possibility of being canceled. Many stories have surfaced of his inappropriate behavior, both on and off screen. It seems as though Letterman used a nice guy persona to mask his dark side, essentially hiding in plain sight.
In addition to being inappropriate - and often downright creepy - towards women, his awkward interviews extend towards men, with a number of his chats with male guests leaving us cringing. Whether it's reflective of his comedic style or something far more troubling, here are the top 10 most awkward David Letterman interviews ever.
10 Jennifer Aniston
Letterman's interview with the much loved Friends star is beyond awkward and creepy. When she recalls an instance of encountering a fan in a steam room, the host asks a series of inappropriate questions, such as whether she was naked, essentially attempting to conjure a pornographic lesbian fantasy.
Thereafter, he constantly edges closer and closer towards Aniston despite her continued and obvious resistance, and he even tries to kiss her. She rejects his advances, but the ultimate "wtf" moment comes when he starts sucking on her hair. Aniston is left looking humiliated. Worst of all, he blames her for the uncomfortable ordeal, brushing off her discomfort by saying "how do you think I felt?", a common tactic of victim-blaming.
9 Madonna
As soon as Madonna enters, Letterman makes things weird. He insists that she kiss a guy in the audience to which she retorts, "Why are you so obsessed with my sex life?" Unfortunately, Letterman won't relent and keeps goading the pop superstar to kiss a random man. Madonna is visibly uncomfortable. When he expresses his surprise that she didn't give into pressure to appease him, she can no longer contain her composure and snaps, "You are a sick ****."
8 Joaquin Phoenix
The 2009 Joaquin Phoenix interview is awkward in a whole different way, as the actor clearly didn't want to be there. A man of very few words, he gives the host sparse replies to queries and exhibits a number of nervous ticks. This leads Letterman to compare him to the Unabomber.
At the time, Phoenix had famously declared that he was giving up on acting forever, so when Letterman asks him why, he simply says "I dunno." Of course, Joaquin didn't give up on acting, as he recently won an Oscar for Joker, a movie that this interview has been compared to.
7 Catherine Zeta-Jones
When Zeta-Jones appeared on Letterman in 2007, he makes it an awkward occasion from the outset. She recalls a past appearance on the show in which Letterman watched her as she hit golf balls in a low-cut dress: "Or was I dreaming that?" he ponders.
Later, when she discusses a scene in No Reservations in which she swiftly removed a table cloth from under cutlery, he immediately sexualizes her description. This then spurs him to ask if he can "do one thing", but rather than waiting for the actress's consent, he starts stroking her hair and she proceeds to squirm in her seat.
6 Janet Jackson
Famously, Jackson experienced a so-called "wardrobe malfunction" at the Super Bowl in 2004. Shortly afterwards, she was interviewed by Letterman, who insistently provoked her into discussing the incident, much to Jackson's discomfort. As soon as she enters the stage, Letterman points to her low-cut red dress and remarks "that's almost malfunctioning, isn't it?" Jackson looks incredibly self-conscious throughout the interview.
Since the interview resurfaced this year, Twitter users have been quick to defend Jackson against Letterman's inappropriate behavior, with one Tweeting, "I don't know how he gets away with it".
5 Lindsay Lohan
In 2006, Lohan appeared on the show to promote the Robert Altman movie A Prairie Home Companion. The interview is increasingly awkward as the host keeps pressuring Lohan to divulge details about her love life, which she is not willing to talk about. Embarrassed, she jokes that she wants to leave.
But Letterman continues with the creepiness, asking the then 19-year-old, "We're curiously interested in a lovely younger woman like yourself... What kind of a little shred of a fantasy might we take with us now?"
4 Harmony Korine
Another interview that isn't creepy, but just plain awkward. Why the art-house indie director was invited on Letterman in the first place remains a mystery. Clearly, Letterman wasn't prepared for Harmony Korine's quirky personality. The squeaky-voiced director first appeared on the show in 1995 when he was 22, having written the controversial Larry Clark movie Kids.
He comes across as self-conscious and childlike, going on frequent tangents that range from discussing Hassidic Jewish people in his neighbourhood to telling a random Aspirin-based joke. The interview is truly the epitome of awkwardness, with the host not quite knowing what to do with the apprehensive Korine. "I could pretty much have this conversation with myself," Letterman jokes.
3 Claire Danes
In 1995, Danes appeared on the show to promote her movie Home for the Holidays. Letterman is oddly obsessed with discussing Danes' age, asking whether she is a girl or a woman. When she states that she is a teenager on the verge of womanhood, Letterman creepily responds, "Well, I hope it happens here tonight!" Ogling an underage girl and repeatedly obsessing over her age simply would not fly today.
2 Paris Hilton
The heiress appeared on the talk show in 2007 and was supposed to be promoting her new perfume. Instead, Letterman focused on her legal troubles, almost immediately asking her if she liked being in jail (Hilton had spent 45 days in jail for violating her probation).
She has since publicly condemned Letterman. On her podcast, This is Paris, she said, "It was like he was purposely trying to humiliate me. During commercial breaks I would look at him like, 'Please stop doing this. You promised me you wouldn't talk about this.'" But the host ignored her pleas and continued to ask her a series of invasive questions.
1 Taylor Swift
Time and time again, Letterman has shown himself to be obsessed with women's scents, frequently commenting on how "wonderful" female guests smell. But when Taylor Swift appeared on his show in 2010, Letterman got weirdly specific about her scent. In addition to once again pressuring his female guests into discussing their love lives, he tells the then 20-year-old that, "you smell like expensive wood." After witnessing the shock on Swift's face, he doesn't relent, continuing to discuss the specifics of her supposed woody scent.