Top 10 David Letterman Interviews That Haven't Aged Well
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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