He said WHAT?! Welcome to WatchMojo, and today we’re counting down our picks for the most noteworthy celebrity interviews on David Letterman’s late-night shows that are now uncomfortable to watch.
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00:00 "You can't get through a show without talking about me, or thinking about me."
00:05 Welcome to WatchMojo, and today we're counting down our picks for the most noteworthy celebrity
00:10 interviews on David Letterman's late night shows that are now uncomfortable to watch,
00:14 either due to the host's inappropriate behavior or that of the interviewee.
00:18 "Dave, you're gonna make me read this.
00:20 I wanna put all that behind me."
00:24 Number 10.
00:25 Crispin Glover.
00:26 Known for his roles in Friday the 13th, The Final Chapter, and Back to the Future, Crispin
00:31 Glover was an actor on the rise in the 1980s.
00:34 On January 28, 1987, Glover appeared on Late Night to promote his new film, River's Edge.
00:40 "Uh, things going alright this summer?"
00:43 "I'm having a very good summer."
00:45 Surprisingly, the actor arrived still in character from the movie, donning mismatched clothes,
00:51 platform shoes, and a distracting wig.
00:54 Glover's behavior throughout the interview was erratic, as he read critical media reviews
00:58 about himself to a confused Letterman.
01:01 "Though his bark is actually worse than his dot, dot, dot, you get the point."
01:06 "Paul, anything you'd like to add here?"
01:10 Things took a bizarre turn when he flexed his bicep, offered to arm wrestle Letterman,
01:15 then executed a karate kick that narrowly missed his face.
01:18 "I can kick."
01:21 That proved too much for the host, who walked off the stage, abruptly concluding the interview.
01:30 Number 9.
01:31 Catherine Zeta-Jones
01:33 On July 25, 2007, Welsh actress Catherine Zeta-Jones made an appearance on The Late
01:38 Show to promote her upcoming film, No Reservations.
01:41 "Why are you so mad at me?"
01:42 "I'm not mad at you."
01:43 It didn't take long for the interview to go on a sexual tangent.
01:47 At first, Letterman recalled Zeta-Jones' previous appearance on the show, where he
01:51 watched her hit golf balls in a low-cut dress.
01:54 He then wondered aloud if it was just a figment of his imagination.
01:58 As Zeta-Jones discussed a scene from No Reservations, the host quickly injected a sexual undertone
02:04 to it, then asked if he could do, quote, "one thing."
02:07 "Do you mind if I just do one thing?"
02:09 "What?"
02:10 Letterman began stroking the actress' hair.
02:13 Judging by her facial expression, it was evident that this gesture was far from appreciated.
02:19 Number 8.
02:20 Uma Thurman
02:21 When actors appear on late-night talk shows to promote their projects, they typically
02:25 aren't looking to flirt with the hosts.
02:27 "Have you ever been married yourself?"
02:28 "She shoves him off, uh, um, onto the person he belongs with."
02:33 "Okay, I'm not talking about the film now."
02:34 That didn't seem to matter to Letterman during Uma Thurman's 1995 visit to discuss
02:38 her role in A Month by the Lake.
02:40 As the interview progressed, Letterman steered the conversation from the film to her personal
02:45 life and inquired if she had ever dated older men.
02:48 He then asked the 25-year-old Thurman if she'd ever been with various age groups, and included
02:53 his own age at the time.
02:55 "What's the oldest man you've ever gone out with?"
02:57 "Um…"
02:58 "You're 25.
02:59 You ever been out with a guy 30?"
03:00 "Yes."
03:01 "35?"
03:02 "Yes."
03:03 "48?"
03:04 "No."
03:05 The actress could only respond with little more than an embarrassed laugh, but she clearly
03:09 wanted to keep discussing the film rather than being caught up in an awkward, flirtatious
03:13 moment.
03:14 "Well, it's a lovely, lovely piece of work, as are you."
03:18 Number 7.
03:19 Claire Danes
03:20 Back in 1995, Claire Danes was a precocious teenager just starting to make a name for
03:25 herself in Hollywood.
03:26 "You know, you and I have something in common.
03:27 You must know about this by now, don't you?"
03:28 "We have the same birthday."
03:29 "We share a birthday, that's right."
03:30 "April 12th."
03:31 "April 12th."
03:32 That year, she appeared as a guest on The Late Show to promote the family drama Home
03:37 for the Holidays.
03:38 The interview started off pretty normal, but things began to get weird when Letterman was
03:42 made aware of the actress' age.
03:43 "When were you born?"
03:44 "I'm 16, 1979.
03:45 I just missed 1980."
03:49 From there, he delved into probing questions about her romantic relationships.
03:53 "I have a boyfriend now, so…"
03:54 "What's his name?"
03:55 It's safe to say that such a line of questioning would be deemed highly inappropriate today.
04:00 Number 6.
04:01 Justin Bieber
04:02 Things took quite the physical turn in this June 2012 interview with Canadian pop star
04:06 Justin Bieber.
04:07 Bieber had just released his third studio album Believe and commemorated the occasion
04:12 by getting a tattoo of the album's title on his left arm.
04:16 This certainly didn't please Letterman, who disapproved of body ink.
04:20 "How does that help how you look to have a tattoo?"
04:22 After grilling the artist about his decision to get the tattoo, Letterman suddenly grabbed
04:27 him and tried to scrub it off his arm.
04:29 "Hey, hey, hey, hey.
04:31 Hey, this is a brand new."
04:32 This attempt visibly distressed Bieber, who yelled out in protest, stating that the tattoo
04:37 was freshly done.
04:39 To his credit, Letterman later approached Bieber and tried apologizing for his behavior,
04:43 but the singer assured him it was all water off a tattooed duck's back.
04:47 "It was awful.
04:48 And I felt awful about it.
04:51 And then we were reassured that he was okay."
04:53 Number 5.
04:54 Janet Jackson
04:55 In 2004, Janet Jackson experienced the now infamous wardrobe malfunction while performing
05:00 alongside Justin Timberlake at the Super Bowl halftime show.
05:03 "So I take me, no disrespect.
05:06 I don't mean no harm."
05:08 The incident sparked widespread media attention for weeks afterwards.
05:12 During this period, Jackson appeared on The Late Show to promote her album Demi to Joe
05:17 and faced a barrage of questions about the mishap.
05:19 "You didn't know it was going to happen.
05:21 So it came as a complete surprise to you."
05:24 Letterman grilled the artist about whether or not the malfunction was pre-planned, a
05:28 claim that both parties had denied multiple times.
05:31 Jackson repeatedly refuted this claim and begged Letterman to move on to another topic
05:35 to no avail.
05:36 "Oh God.
05:37 Can we talk about something else please?"
05:41 The entire exchange is uncomfortable to watch, so we can only imagine what it must have been
05:46 like for Jackson herself.
05:47 "Why are we talking about this right now, David?"
05:48 "What would you like to talk about?"
05:55 Number 4.
05:56 Lindsay Lohan
05:57 Everyone knows Lindsay Lohan went through a challenging period in the late 2000s and
06:01 early 2010s.
06:02 "Aren't you supposed to be in rehab now?"
06:05 "Do you not watch anything that goes on?"
06:08 Her personal troubles became comedy fodder for the media, and not much had changed by
06:12 the time she appeared on The Late Show in 2013.
06:15 Lohan was there to promote the horror-comedy Scary Movie 5, but Letterman was more interested
06:21 in her trips to rehab.
06:22 "What are they going to work on when you walk through the door?"
06:25 "We didn't discuss this in the pre-interview."
06:29 Despite multiple pleas from Lohan to "stay on the positive," Letterman kept prodding,
06:35 eventually forcing her to reveal the date of her return to rehab.
06:39 After making multiple jokes at her expense, Letterman then tried to correct course by
06:43 praising her for still coming on the show despite his endless mockery.
06:47 This caused the actress to become emotional.
06:49 "No, I love seeing you."
06:51 "I love seeing you, honestly."
06:53 Number 3.
06:54 Paris Hilton
06:55 In 2007, Paris Hilton was sentenced to 45 days in jail for violating her probation from
07:00 a previous DUI charge.
07:02 Later that year, she went on The Late Show to discuss her new perfume, on the condition
07:07 that her incarceration would not be brought up.
07:09 "How much time do you spend in New York City?
07:11 A lot?"
07:12 "Not as often as I'd like."
07:13 It didn't take long for David Letterman to breach this agreement.
07:16 Shortly after Hilton sat down, Letterman pressed her about her time behind bars.
07:20 "Uh, how'd you like being in jail?"
07:23 "I'm not going to do it."
07:25 Although she indulged the host, Hilton was clearly uncomfortable with his line of questioning,
07:30 and highlighted that it was a traumatic experience for her.
07:32 "I feel like I can do anything else."
07:34 "You can survive anything, sure."
07:35 "Yes, definitely."
07:36 Years later, she reflected on the interview on her podcast, stating that it felt like
07:40 a cruel and intentional attempt by Letterman to humiliate her.
07:44 "It was just very cruel and very mean."
07:46 Number 2.
07:47 Madonna
07:48 There is one word you cannot say on network television.
07:52 Yet during this infamous 1994 Late Show interview, Madonna managed to say it a whopping 14 times.
08:03 Things immediately went south as soon as the interview began.
08:07 After Letterman introduced Madonna in a somewhat derogatory fashion, he then urged her to kiss
08:12 a man in the audience.
08:14 That led to the first of many F-bombs.
08:22 From that point on, the two entered a sort of sexual innuendo tug of war, with Madonna
08:27 leading the charge and dropping several expletives along the way.
08:42 Despite her allotted time ending, the pop star defiantly remained on set, resulting
08:46 in some audience members heckling her to leave.
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09:09 Number 1.
09:10 Jennifer Aniston
09:12 Invading someone's personal space is one thing, but licking a part of their body, especially
09:17 without their consent, is a different level of intrusion.
09:22 That's exactly what unfolded during this strange 1998 interview with Jennifer Aniston.
09:27 The actress was on the Late Show to promote her new film, The Object of My Affection,
09:32 but instead became the object of an unsettling interaction.
09:37 During the interview, Letterman suddenly drew closer to Aniston, who appeared visibly uncomfortable,
09:43 and proceeded to suck on a strand of her hair.
09:49 He then handed her a tissue to wipe the saliva off.
09:52 In addition to being creepy and frankly disgusting, it's a completely unnecessary moment that
09:57 is sure to leave you wondering "why?"
10:06 What other David Letterman interview left you feeling uneasy?
10:10 Let us know in the comments below.
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