David Letterman’s 5 most controversial interviews as backlash erupts

Earlier this week, a controversial interview by David Letterman with Lindsay Lohan resurfaced on Twitter.

The viral clip, from 2013, shows Letterman probing Lohan about her struggles with addiction.

The Mean Girls star appears uncomfortable keeps trying to deflect back to the original topic of discussion, her new film.

After Letterman asks if she is supposed to be in rehab, Lohan informs the host that she is due to check into a facility in the near future.

“What are they rehab-ing? What is on their list? What are they going to work on when you walk through the door?” replies Letterman, as Lohan appears more and more uneasy.

Now, more videos have reemerged of Letterman’s interactions with female guests.

Sucking Jennifer Aniston’s hair in 1998

Friends star Jennifer Aniston was interviewed by Letterman on The Late Show in 1998.

In the clip, they’re discussing Aniston’s fan base – ironically, about awkward encounters with fans – before Letterman jumps up, wraps one hand around Aniston’s neck, and sucks her hair.

Like a noodle.

Aniston looks both confused and concerned – and after returning to his seat, Letterman offers her a tissue to wipe the saliva from her hair.

Asking about Christina Aguilera’s piercings in 2004

When ‘Genie in a Bottle’ singer Christina Aguilera went onto his show in 2004, Letterman did not want to talk about her musical success – but her body piercings.

After calling her “terribly exotic”, he then wanted to know “exactly” where she is pierced.

The singer then asked Letterman to change the subject. After a conversation like that, that’s the most polite thing she could ask him to do. 

Quizzing Paris Hilton about prison in 2007 

Letterman’s interview with Lindsay Lohan shows that he doesn’t deal well with difficult subjects.

In a 2007 interview with Paris Hilton, Letterman turns to the socialite and asks her about her stint in prison after a reckless driving incident. 

She quickly tells Letterman it was “very traumatic”, but that she’s now moving forward with her life.

Then, when an audience member shouted to tell Lohan that they loved her, Letterman clearly hadn’t moved on, and asked Lohan if she’d “met them in prison”.

“You’re hurting my feelings, can we please stop talking about it,” responded Hilton.

Letterman apologised to Hilton in a later appearance on his show in 2008, acknowledging he had “offended” her and “felt horrible” about it.

“I’m terribly sorry,” he said. “How did you feel? What did I do? You didn’t want to talk about [it] but I kept pressing you on it, didn’t I?”

Being called a ‘sick f***’ by Madonna in 1994

In case you’ve reached the end of this list with a yearning to see some form of retribution upon Letterman, you may be happy to know that Madonna called Letterman a sick “f*** live” on air after his questions got too much for her.

Letterman told Madonna (imagine telling Madonna what to do?) to go and “go kiss the guy in the audience, it would knock him out.”

Madonna refused, and Letterman replied: “A lot of people would cave into the pressure and say ‘oh alright and go out there and get it over with.”

“Yeah well I’ve never succumbed to peer pressure,” Madonna responds, following up with: “Incidentally, you are a sick f*** … I don’t know why I get so much sh**.”

Letterman’s representatives have been contacted for further comment.

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