Top 10 David Letterman Interviews That Haven't Aged Well
#10: Crispin Glover
Known for his roles in “Friday the 13th: The Final Chapter” and “Back to the Future,” Crispin Glover was an actor on the rise in the 1980s. On July 28th 1987, Glover appeared on “Late Night” to promote his new film “River's Edge”. Surprisingly, the actor arrived still in character from the movie, donning mismatched clothes, platform shoes and a distracting wig. Glover’s behavior throughout the interview was erratic, as he read critical media reviews about himself to a confused Letterman. Things took a bizarre turn when he flexed his bicep, offered to arm wrestle Letterman, then executed a karate kick that narrowly missed his face. That proved too much for the host, who walked off the stage, abruptly concluding the interview.
#9: Catherine Zeta-Jones
On July 25th 2007, Welsh actress Catherine Zeta-Jones made an appearance on the “Late Show” to promote her upcoming film “No Reservations”. It didn’t take long for the interview to go on a sexual tangent. At first, Letterman recalled Zeta-Jones’ previous appearance on the show where he watched her hit golf balls in a low-cut dress. He then wondered aloud if it was just a figment of his imagination. As Zeta-Jones discussed a scene from “No Reservations,” the host quickly injected a sexual undertone to it, then asked if he could do “one thing”. Without even waiting for her permission, Letterman began stroking the actress’ hair. Judging by her facial expression, it was evident that this gesture was far from appreciated.
#8: Uma Thurman
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When actors appear on late-night talk shows to promote their projects, they typically aren’t looking to flirt with the hosts. That didn’t seem to matter to Letterman during Uma Thurman’s 1995 visit to discuss her role in “A Month by the Lake”. As the interview progressed, Letterman steered the conversation from the film to her personal life and inquired if she had ever dated older men. He then asked the 25-year-old Thurman if she’d ever been with various age groups, and included his own age at the time. The actress could only respond with little more than an embarrassed laugh, but she clearly wanted to keep discussing the film rather than being caught up in an awkward flirtatious moment.
#7: Claire Danes
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Back in 1995, Claire Danes was a precocious teenager just starting to make a name for herself in Hollywood. That year, she appeared as a guest on the “Late Show” to promote the family drama “Home for the Holidays”. The interview started off pretty normal, but things began to get weird when Letterman was made aware of the actress’ age. From there, he delved into probing questions about her romantic relationships. At one point in their conversation, Danes mentioned that she was just on the brink of womanhood, prompting a somewhat unsettling response from Letterman. Safe to say, such a line of questioning would be deemed highly inappropriate today.
#6: Justin Bieber
Things took quite the physical turn in this June 2012 interview with Canadian pop star Justin Bieber. Bieber had just released his third studio album “Believe” and commemorated the occasion by getting a tattoo of the album’s title on his left arm. This certainly didn’t please Letterman, who disapproved of body ink. After grilling the artist about his decision to get the tattoo, Letterman suddenly grabbed him and tried to scrub it off his arm. This attempt visibly distressed Bieber, who yelled out in protest, stating that the tattoo was freshly done. To his credit, Letterman later approached Bieber and tried apologizing for his behavior but the singer assured him it was all water off a tattooed duck’s back.
#5: Janet Jackson
In 2004, Janet Jackson experienced the now infamous “wardrobe malfunction” while performing alongside Justin Timberlake at the Super Bowl halftime show. The incident sparked widespread media attention for weeks afterwards. During this period, Jackson appeared on the “Late Show” to promote her album “Damita Jo” and faced a barrage of questions about the mishap. Letterman grilled the artist if the malfunction was pre-planned, a claim which both parties had denied multiple times. Jackson repeatedly refuted this claim and begged Letterman to move on to another topic, to no avail. The entire exchange is uncomfortable to watch, so we can only imagine what it must have been like for Jackson herself.
#4: Lindsay Lohan
Everyone knows Lindsay Lohan went through a challenging period in the late 2000s and early 2010s. Her personal troubles became comedy fodder for the media, and not much had changed by the time she appeared on the “Late Show” in 2013. Lohan was there to promote the horror comedy “Scary Movie 5” but Letterman was more interested in her trips to rehab. Despite multiple pleas from Lohan to “stay on the positive,” Letterman kept prodding, eventually forcing her to reveal the date of her return to rehab. After making multiple jokes at her expense, Letterman then tried to correct course by praising her for still coming on the show despite his endless mockery. This caused the actress to become emotional.
#3: Paris Hilton
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In 2007, Paris Hilton was sentenced to 45 days in jail for violating her probation from a previous DUI charge. Later that year, she went on the “Late Show” to discuss her new perfume, on the condition that her incarceration would not be brought up. It didn’t take long for David Letterman to breach this agreement. Shortly after Hilton sat down, Letterman pressed her about her time behind bars. Although she indulged the host, Hilton was clearly uncomfortable with his line of questioning and highlighted that it was a traumatic experience for her. Years later, she reflected on the interview on her podcast, stating that it felt like a cruel and intentional attempt by Letterman to humiliate her.
#2: Madonna
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There is one word you cannot say on network television. But during this infamous 1994 “Late Show” interview, Madonna managed to say it a whopping 14 times. Things immediately went south as soon as the interview began. After Letterman introduced Madonna in a somewhat derogatory fashion, he then urged her to kiss a man in the audience. That led to the first of many F-bombs. From that point on, the two entered a sort of sexual innuendo tug of war, with Madonna leading the charge and dropping several expletives along the way. Despite her allotted time ending, the pop star defiantly remained on set, resulting in some audience members heckling her to leave.
#1: Jennifer Aniston
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Invading someone’s personal space is one thing, but licking a part of their body, especially without their consent, is a different level of intrusion. That’s exactly what unfolded during this strange 1998 interview with Jennifer Aniston. The actress was on the “Late Show” to promote her new film “The Object of My Affection” but instead became the object of an unsettling interaction. During the interview, Letterman suddenly drew closer to Aniston, who appeared visibly uncomfortable, and proceeded to suck on a strand of her hair. He then handed her a tissue to wipe the saliva off. In addition to being creepy and frankly disgusting, it’s a completely unnecessary moment that is sure to leave you wondering: “why?”