Britney Spears documentary leads fans to resurface David Letterman uncomfortable interviews with female stars

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David Letterman’s critics have been resurfacing past interviews in which the host seemingly made some female guests uncomfortable in the past.

The renewed attention of Letterman’s treatment of his guests while he was the host of “The Late Show” comes after a resurfaced clip of him interviewing Lindsay Lohan in 2007 went viral. In the clip, the host continues to ask the young star about her upcoming stint in rehab until she eventually becomes so uncomfortable she starts to cry. 

While that particular interview appeared to have the host going off-book — with Lohan at one point saying that they didn’t discuss the topic in the pre-interview — it’s hardly the first time that Letterman has had friction with guests.

A rep for Letterman had “no comment” when reached by Fox News.

Paris Hilton

Paris Hilton waded her way through questions about her time in jail on Letterman’s show.

During a 2007 chat with reality star Paris Hilton, Letterman makes her visibly uncomfortable when he continues to probe her with questions about some time she spent in jail after violating her probation for reckless driving.

According to Glamor, the interview sees Letterman ask “How did you like being in jail?” almost immediately when Hilton takes the stage as the audience applauded wildly. The outlet reports that Hilton handled herself well and may have been expecting the uncomfortable questions about jail but that Letterman continued to press her on the subject.

“Obviously it was a very traumatic experience but I did it,” she said. “I feel like I can do anything now.” 


Eventually, she got the host to move on to promote her perfume line, after flat out telling him that she would not answer any more of his questions about jail. After that, the outlet reports he lectured her about her status as a role model for youths. 

“Now you’re making me sad I cam here,” Hilton eventually said. “You’re hurting my feelings.” 

Janet Jackson

Janet Jackson apologized for the 2004 wardrobe malfunction but was ultimately blacklisted by CBS and MTV.

After an illustrious career, it’s not surprising that Janet Jackson was upset to appear on Letterman in 2004 and find that all the host wanted to talk about was her infamous wardrobe malfunction at the Super Bowl Halftime show that year. 

According to Entertainment Weekly, the host mocked her outfit on the show by saying that the low-cut top she was wearing was “almost malfunctioning.” 

The artist was bleeped on the broadcast for saying “Oh Jesus” when he brought up the halftime show gaffe that saw her exposed breast revealed on TV. 


The interview got somewhat uncomfortable when she tried to shut down Letterman’s line of questioning by explaining that she had nothing to say about the incident that she hadn’t already mentioned countless times during a recent press tour for her upcoming album.

Christina Aguilera

Aguilera was asked about her piercings on Letterman in 2004.
(Getty Images)

In response to the video about Lohan, one Twitter user resurfaced a clip of Aguilera from 2004 in which Letterman continued to ask the actress uncomfortable questions about her body piercings, trying desperately to get her to talk about ones in “special areas.” 

When she came out, he immediately told her she looked “terribly exotic” and probed her with more questions about her body modifications.

“How did this become about my piercings,” she says at one point.


The artist gets a little embarrassed when the audience uproariously applauds at her admitting that she’s done getting piercings. 

“Maybe we should change the subject,” she says as Letterman continues to ask follow-ups.

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