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Our salute to the funny men and women of post-prime time

Shaun Harrison
1 of 11 Margaret Norton/NBCU Photo Bank

The Dancing Itos

Yes, Jay Leno went to this well about a half-dozen times too often. But the "Dancing Itos" — a troupe of hoofers made up to look like the judge presiding over the all-too-real double murder trial of O.J. Simpson —aptly captured what a media circus that courtroom spectacle had become.
2 of 11 Alice S. Hall/NBCU Photo Bank

Bette Midler Serenades Johnny Carson

On May 21, 1992, Carson's second-to-last Tonight Show broadcast (his final show had no guests), Midler sang an emotional rendition of the pop standard "One For My Baby (and One More for the Road)" for the talk-show legend. Producers cut to an unprecedented camera angle — a view of Johnny from behind Midler — that showed a teary-eyed Carson. When Midler finished, she rushed over to Carson, presented him with a lei and ran backstage, visibly shaken. She won an Emmy for her performance that night.
3 of 11 Alan Singer/CBS

Drew Barrymore Flashes David Letterman

Before she was America's sweetheart, bad girl Barrymore flashed Letterman during an impromptu striptease atop his desk during a 1995 visit to the show. Though Barrymore's back is to the camera, seeing the stunned look on Letterman's face is almost worth missing the view.
4 of 11 Dana Edelson/NBC

D**k in a Box

This SNL Digital Short totally made up for the many others that were, shall we say, less than hysterical. Justin Timberlake and Andy Samberg teamed up for this dirty ditty (and the awesome retro-vibed video), further solidifying JT as SNL's most valuable host this decade and Samberg as "that guy in all the digital shorts."
5 of 11 CBS/Landov

Oprah Finally Appears on Letterman

Oprah, Dave. Dave, Oprah. The 16-year-old alleged cold war between the two ended Dec. 1, 2005, when O stopped by to promote The Color Purple musical. The result: 13.45 million viewers. "It's really over, whatever you thought was happening," she said.
6 of 11 D. Herrick/; Dana Edelson/NBCU Photo Bank; J. Kempin/

The Other Guys

Late night hosts can't do it all alone. Carson and Conan turned to awesome sidekicks like Ed McMahon and Andy Richter respectively, while Letterman sometimes took a back seat to Chris Elliot's recurring oddball characters and ridiculous parodies.
7 of 11 Dana Edelson/NBC

Tina Fey as Sarah Palin on SNL

Fey's Palin impression was more than just hauntingly accurate — it also set the tone for a rip-roaring new season of SNL that breathed new life into the show and helped it regain its former cultural relevance.
8 of 11 screengrab courtesy CBS

Cher Tells Off David Letterman

In Cher's first visit to Letterman's show (May 21, 1986), the usually quick-witted Letterman's game was thrown by Cher's straightforward declaration that she never wanted to appear on the show because she thought he was an "a--hole." The conversation gets increasingly awkward from there. By the end of the segment, Cher calls him "cute" and writes a secret note to him on his interview cards. It's unclear if they're flirting or fighting at this point, but it's nonetheless hard to look away.
9 of 11 Stan Honda/Getty Images; Dana Edelson/NBC

Conan Embraces his Lookalike

Before stars campaigned for Obama, Conan O'Brien stumped for Tarja Halonen, his Finnish doppelganger running for presidential re-election in 2006. Oh, she's also a woman. Aware of his place in political history, O'Brien even made the trek to visit Madame Prez.
10 of 11 John Paul Filo/CBS

John McCain's Late Show Mea Culpa

It's one thing to lie. It's another to get caught doing so on national television. But it's also an entirely other thing to face your gaffe head on and take your lumps, especially when David Letterman is the one handing them out. McCain really is an American hero.
11 of 11 Dana Edelson/NBCU Photo Bank

Conan vs. Jon Stewart vs. Stephen Colbert

It was a meeting of late-night greats and fists in February 2008 when Jon Stewart and Stephen Colbert dropped by to duel with Conan O'Brien, West Side Story style, over who "made" Mike Huckabee's campaign. Totally trumps that Letterman-McCain "feud."