Top 10 Late Night Moments With David Letterman

David Letterman

Comedy staple and late-night icon David Letterman is celebrating his 30th year on late-night television this evening.

Letterman started his after comedy career on a short-lived morning show called “The David Letterman Show” which was critically acclaimed but not a ratings success.

Two years later came the big NBC gig, “Late Night with David Letterman.” The show was a huge hit and Letterman was responsible for some of the best comedy bits of all time. “Late Show” saw the creation of such classic routines like “Stupid Pet Tricks,” “Stupid Human Tricks,” and “Small Town News.”

But when Johnny Carson retired from “The Today Show” in 1992 and the gig went to Jay Leno, Letterman moved to CBS and started a late night rivalry that provided for some awesome (and sometimes even awkward) laughs.

Celebrities, comedy bits, and surprising emotional moments are what make Letterman’s show so fun to watch. 

One of Letterman's new bits on 'The Late Show with David Letterman' was also one of the most bizarre. This bit saw Letterman take different items and put them in water to see if they'll float or not. It was preceeded with a hard rock theme by sidekick and music legend Paul Schaffer and it spawned a board game of the same name.

Though how this bit actually works as a board game is still a mystery.

9. Crispin Glover gets physical

'Back to the Future' star Crispin Glover always looked a bit strange. But it wasn't apparent how strange he really could be until he made his first appearance on 'The Late Show' in 1987.

While promoting his film 'River's Edge,' Glover made his appearance as a character from one of his other movies, 'Rubin and Ed.' A movie which would not be released for another four years.

During the weird interview, Glover challenged Letterman to an arm-wrestling match and proceeded to do a roundhouse kick which almost his Letterman in the face. After commercial break, Glover was gone.

Awkward...

When George W. Bush was in office, Letterman used his two-term presidency as comedy gold. He didn't have to do much for this particular sketch.

'Great Moments' took bits of different speeches and press conferences by the former president and picked out the most embarrassing moments or the scenes that made Bush look as ridiculous as possible.

In early 2009, right before President Obama's inauguration, Letterman showed the grand finale of 'Great Moments.' Check it out.

7. Letterman's first after show after heart surgery

In early 2000, Letterman had to put his show on hiatus after finding out needed to get heart bypass surgery. When he was finally able to come back to 'The Late Show' five weeks later, Letterman started out his first episode by bringing onto the set all of the nurses, doctors and hospital staff who were involved with his surgery and recovery.

The comedian started the show by joking, 'Wait 'till you hear what happened to me.' Then he publicly thanked all of the medical staff by saying that all of them 'saved his life.' What's better than being heartfelt and hilarious?

When Letterman hosted 'Late Night with David Letterman,' one of his most popular and random bits was 'Throwing stuff off of a five-story tower.'

It is literally exactly what it sounds like.

The best way to explain how funny and strange it is would be to just watch the clip. Best item thrown off the building? 'Some balloons filled with guacamole.'

See? Random.

5. Drew Barrymore does a stripper dance

The young starlet from 'ET' and 'Charlie's Angels' hasn't always been the innocent sweet girl from the movies. She was once a wild child with one memorable appearance on 'The Late Show' in 1995.

To celebrate Letterman's birthday, Barrymore got up on his desk, did a sultry dance and flashed the host--all while the cameras were rolling.

4. Madonna gives Letterman a whole lot of lip

In 1994, Madonna appeared on Letterman's show and she was in a mood.

Throughout the interview, Madge was difficult when Letterman asked his questions, insulted him on multiple occasions and made a whole lot of dirty innuendos.

The host had his fair share of comebacks, but the episode was filled with both uncomfortable and hilarious moments.

3. Paris Hilton

It's hard to talk about Paris Hilton without making a joke. Ask Letterman.

Madonna made a joke during her interview that Letterman had 'gotten soft' during his interview. But the 'Late Show' host definitely did not hold back any punches with the heiress.

Hilton had recently been released from prison and there was no way Letterman wasn't going to bring that up. After asking some boring questions about cities, Letterman started out his barrage by asking, 'How'd you like being in jail?'

He went on to ask excrutiatingly detailed questions and proved to be one of the best episodes ever.

2. Joaquin Phoenix goes crazy

Joaquin Phoenix came on 'The Late Show' to promote 'Two Lovers,' which was to be his last movie ever after he announced his plan to pursue a career in hip hop music. Sporting a riduculous beard, disheveled hair and sunglasses, the actor barely answered the host's questions.

As we all found out later on, the appearance was part of an elaborate act for a faux-documentary starring Phoenix called 'I'm Not Here.' But it didn't make the interview any less awkward.

One of the best lines from the interview came from Letterman at the very end when Phoenix had spit his gum out on the host's desk, 'Joaquin, I'm sorry you couldn't be here tonight.'

It all started during 'Late Night with David Letterman.'

This daily comedy bit would almost always be a joke about some timely event. Throughout the years, different public figures have even appeared on 'Late Night' and 'The Late Show' to read the infamous 'Top 10 Lists.'

Some of the best lists came from political elections or celebrity blunders/scandals like 'The Top 10 Messages Left on Joe the Plumber's Answering Machine' or 'Top 10 Papers Written by Brooke Shields at Princeton' and many, many more.

Here's one that premiered around the release and rising popularity of 'Napoleon Dynamite.'

Letterman has had some pretty powerful celebrity guests over his 30-year career.

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