David Letterman’s 10 Most Memorable TV Moments From Late Night!

Lindsay Lohan – 2013

Letterman surprised the troubled star by asking about her addictions and personal problems, which Lindsay noted, "we didn't discuss in the pre-interview." But the host redeemed himself by telling the actress he admired her guts to come on the show even after all his jokes at her expense. The sentiment made Lindsay cry.

Madonna – 1994

The superstar punished the host for making jokes about her promiscuity by cursing throughout the interview and detailing her active sex life. Letterman soon realized he had lost control of his guest.

Crispin Glover – 1987

The eccentric actor was on the show to promote his film River's Edge, and acted so strangely — he challenged Letterman to an arm wrestling contest — that the host actually walked off stage, forcing producers to cut to commercial.

Drew Barrymore – 1995

In celebration of the host's 50th birthday, Drew danced atop Letterman's desk before flashing him her bare breasts (her back was to the camera). The comedian's face afterwards is truly priceless!

John McCain – 2008

The former Republican presidential candidate canceled his appearance at the last minute, citing a financial crisis in D.C. that needed his immediate attention. However, Letterman found out during a broadcast that John had managed to squeeze in a TV interview with Katie Couric before leaving, giving him a whole range of new material. The politician tried to make it up to Letterman by appearing on his show a month later.

Farrah Fawcett – 1997

The blonde bombshell appeared to be drunk, high or both during her interview with Letterman. She was spacey and disoriented, and explained she arrived late to the show because, "Everyone in New York loves me!"

Paris Hilton – 2007

The heiress appeared on the show right after her jail stint, and Letterman made it clear that was ALL he wanted to talk about. After being asked numerous questions about her life behind bars, Paris declared, "I'm not answering any more questions about it. I’m here for my clothing line, my movie and my perfume." After a short pause, Letterman came back with, "How did you like jail?"

Joaquin Phoenix – 2009

The actor debuted a new look on Letterman, appearing on air with a thick beard, messy hair and participating in a truly bizarre interview. At one point, he drank the host's coffee and stuck his used gum onto the Late Show desk. This was supposedly all a publicity stunt for the film, "I'm Still Here," but five years later, we still don't get it.

Peter O'Toole – mid '90s

The famed actor rode into his interview on a camel, all while smoking a cigarette. He later attempted to feed beer to the animal.

First show following the 9/11 terrorist attacks – 2001

He was the first late night host to return to television after 9/11, and the way Letterman handled his monologue that night — with heartfelt honesty and little jokes to alleviate the tension — set the precedent for everyone else.