04:27 PM EDT 08/18/2015

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David Letterman

Tina Fey Strips to Her Spanx to Send David Letterman Off in Style (or Lack Thereof)

Tina Fey Strips to Her Spanx to Send David Letterman Off in Style (or Lack Thereof)

Originally posted 05/08/2015 10:25AM

The comedian refuses to wear another dress after Dave goes off the air

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Happy 54th Birthday, George Clooney! Flash Back to His Very First Letterman Appearance (VIDEO)

Originally posted 05/06/2015 03:10PM

Raise a glass to George Clooney's 54th birthday!

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Late Show With David Letterman

David Letterman Jokes That He's the Father of Reese Witherspoon's Daughter

Originally posted 05/05/2015 11:10PM

[YOUTUBE "MxdGKZewKhw"] Well, she did star in Legally Blonde.

Reese Witherspoon took a minute to catch onto David Letterman's joke when she appeared on the Late Show on Tuesday night.

The talk -how host was marveling at a sweet pic the Hot Pursuit star had shared on Instagram of her look-alike 15-year-old daughter, Ava, when the star revealed that Ava "was born the first year I was on this show."

That prompted some awkward throat clearing from Letterman, who said, "Well, that's an interesting coincidence," as the audience laughed.

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Barack Obama and David Letterman Plan Their Retirement Together on Late Show

Originally posted 05/04/2015 08:30PM

[YOUTUBE "xqtO5UI8hR8" "auto"] Barack Obama and David Letterman just decided to become retirement buddies.

The President made his final appearance on the Late Show on Monday, and started making plans to spend some post-presidency bonding time with the talk show host, who's also nearing the end of his tenure.

"I was thinking you and me could play some dominoes together," the President joked when Letterman asked about his plans after leaving the Oval Office.

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Credit: Jeffrey R. Staab/CBS
From EW: Conan O'Brien's Exclusive Love Letter to David Letterman

From EW: Conan O'Brien's Exclusive Love Letter to David Letterman

Originally posted 05/01/2015 05:20PM

"David Letterman disrupted the medium – and that's what made him a legend," O'Brien writes for EW

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Michelle Obama to David Letterman: One of Our Kids Is Going Through Their 'Grumpy Cat' Phase (VIDEO)

Originally posted 05/01/2015 08:50AM

Even the president and his first lady, it seems, are not immune to the terror of teenage hormones.

Michelle Obama stopped by The Late Show on Thursday and commiserated with David Letterman over the "cloud" that sometimes passes over his 11-year-old son, Harry. "All of a sudden, all we do is argue and reason escapes the planet!"

"Yeah, you're in that phase," replied Michelle, assuring him that it does go away, but that she's currently dealing with that situation in the White House – but wouldn't confirm whether it was Malia, 16, or Sasha, 13.

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Credit: CBS
David Letterman: CBS Had 'Good Reason to Fire Me' After My Sex Scandal | David Letterman

David Letterman: CBS Had 'Good Reason to Fire Me' After My Sex Scandal

Originally posted 04/30/2015 11:55AM

As his 33-year-long tenure on late night comes to a close, David Letterman is feeling reflective.

Though he was candid about his sex scandal when it made headlines in 2009 after a blackmail attempt forced his hand, the late-night host has kept mum on the issue since.

In a revealing interview with The New York Times, Letterman, 68, was able to look at the scandal with some distance. "I think [CBS] would have had good reason to fire me," he said, adding that he was "largely ignorant as to what, really, I had done."

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Credit: Jeffrey R. Staab/CBS/Getty
David Letterman: Jimmy Fallon and Jimmy Kimmel Didn't 'Push Me Out' of a Job

David Letterman: Jimmy Fallon and Jimmy Kimmel Didn't 'Push Me Out' of a Job

Originally posted 04/29/2015 10:40AM

The landscape of late night has inarguably changed since David Letterman began hosting Late Night in 1982 and then Late Show in 1993, but he's not ending his 33-year run on a bitter note.

In an interview with The New York Times, Letterman, 68, is not upset about how the format he helped create has changed so drastically with the entry of energetic, Internet-savvy hosts like Jimmy Kimmel and Jimmy Fallon.

"They didn't push me out," he said. "I'm 68. If I was 38, I'd probably still be wanting to do the show," Letterman added, going on to say that the format – "an older guy in a suit" – certainly still seemed "viable" when Jay Leno was still on late night. However, after Leno left The Tonight Show last year, Letterman was suddenly "surrounded by Jimmys," he told the Times.

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Late Show With David Letterman

Robert Downey Jr. Reveals What Happened When He Sang at His Star-Studded Birthday Party

Originally posted 04/24/2015 01:35AM

[YOUTUBE "CMehrZKy6FY"] Robert Downey Jr. knows how to throw an awesome birthday party.

The Iron Man star, who turned 50 on April 4, didn't just hire out an airplane hangar in Santa Monica, California, and fill it with A-list guests including Jennifer Aniston, Reese Witherspoon and Gwyneth Paltrow – he also arranged for some impressive entertainment.

"It was kind of a big deal," he told David Letterman on The Late Show on Thursday.

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