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Unbelievable! 5 Memorable Movie Guests Before David Letterman Retiring Were Unveiled!

Letterman reacts to a bikini-clad Demi Moore in 1995. The actress starred in the film “Striptease” and helped David with his Top Ten list by removing index cards, one by one, revealing the bikini.


Baltimore Ravens defensive tackle Tony Siragusa goes all out with Letterman in 2001.   (BARBARA NITKE )

Singer Janet Jackson points her finger to Letterman in 2004.  (JOHN PAUL FILO )

Pop star Ricky Martin gestures while talking with Letterman in 1999.   (Patrick D Pagnano  )

Former Beatle Paul McCartney makes an appearance in 2009.  (John Paul Filo )

First Lady Michelle Obama stops by in 2012.   (Jeffrey R. Staab )

Actress Lupita Nyong’o giggles with the audience in 2014.   (Jeffrey R. Staab )

Then-Democratic presidential nominee Sen. Barack Obama visits Letterman in 2008.   (Jeffrey R. Staab )

U.S. Olympic men’s slopestyle gold medalist Sage Kotsenburg interviews with Letterman in 2014.   (Jeffrey R. Staab )

Democratic presidential nominee and Vice President Al Gore takes a crack at Letterman in 2000.   (BARBARA NITKE )

Bill Murray takes a “selfie” with singer Lady Gaga and Letterman in 2014.  (Jeffrey R. Staab )

Dan Rather, anchor of the CBS Evening News, is overcome with emotion as he talks with Letterman shortly after the terrorist attacks of Sept. 11, 2001.   (JF Filo )

Actor Bruce Willis, left, laughs along with then-New Jersey Gov. Christine Todd Whitman and Letterman in 1996.   (ALAN SINGER )

Screenwriter Diablo Cody has a chat with Letterman in 2008.   (J.P. Filo )

Republican presidental candidate and Texas Governor George W. Bush poses for photographers with Letterman after concluding taping of a 2000 showing.   (PAUL J. RICHARDS )

Former exotic dancer and “Big Brother” house guest Jean Jordan tells a story to Letterman in 2000.   (BARBARA NITKE )

Actor Joaquin Phoenix waves to the audience in 2009.   (J.P. Filo )

2008 Republican presidential nominee Sen. John McCain gets comfortable with Letterman.

  (J.P. Filo )

The Rev. Jesse Jackson gets serious with Letterman in 1999.   (BARBARA NITKE )

Actor Robin Williams chats with a bearded Letterman in 2008.   (J.P. Filo )

Oliver Gettell

April 4, 2014 11:42 AM PT

The late-night circuit is usually a well-oiled Hollywood hype machine through which movie stars and hot-shot directors can safely plug their latest films. Every once in a while, though, things go off the rails, a phenomenon that seems to happen with a bit more frequency on Letterman, whose arched detachment can allow those moments to play out in all their awkward glory.

In honor of the “Late Show” host’s announcement that he , here are five of the most memorable movie guests to grace Letterman’s couch. If there’s a common thread running through these appearances — other than Letterman’s acerbic wit — it’s that in the world of late-night TV, one doesn’t need an enduring movie to make a lasting impression.

Drew Barrymore

Back in 1995, Drew Barrymore was sporting close-cropped, bleach-blond locks and playing crazy girls in movies like “Mad Love” and “Boys on the Side” when she gave Letterman an infamous birthday present.

After regaling Letterman with tales of a “nude art performance dance place” run by a woman named Ute, the 20-year-old actress , gyrated for a moment and flashed the late-night host, who was rendered briefly, uncharacteristically speechless.

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