At long last, David Letterman to appear on 'Jimmy Kimmel Live!'

Image Credit: Randy Holmes/ABC

Jimmy Kimmel might just be David Letterman’s biggest fan.

“I’d draw Dave’s face on every book cover. I was like a teenage girl in love with him,” Kimmel told The Hollywood Reporter, speaking of his childhood admiration for the late-night host. Well, now that infatuation has finally come to fruition – Letterman has agreed to appear on Jimmy Kimmel Live!

Kimmel’s own late-night talk show will broadcast from the Brooklyn Academy of Music from Oct. 29 to Nov. 2, and Letterman – who turned down an invitation to be Kimmel’s first guest – will join Stephen Colbert, John Stewart, and others opposite Kimmel. Musical acts for the week’s Brooklyn run include Alicia Keys, Sharon Jones and the Dap Kings, and the Avett Brothers.

Of course, it’s nothing new for talk show hosts to appear on each others’ shows. In fact, the world of late-night comedy shows seems like a cozy little town populated by a few marginally handsome men with penchants for self-deprecation. So in light of this news, here are five great show-hopping moments in late-night TV.

5. Jay Leno on Late Night with David Letterman, 1985

This one barely counts — since Leno wasn’t a host yet. But he was a touring comedian, dubbed the “king of the club comics,” and this clip demonstrates his silver-tongued prowess. He bursts onto Letterman’s set and launches into a rapid-fire monologue that lasts for the entirety of his appearance – Letterman can’t get a word in edgewise. Riffing on everything from the Rambo script (“Rambo opens fire; page two, the end”) to estate sales (“The guy had six copies of Playboy and a garden hose”), this is a young, acerbic comic at the top of his game. It’s also worth watching if only for Leno’s tragic melange of pastel ’80s attire.

4. Jon Stewart and Stephen Colbert on Conan, 2011

Stewart and Colbert aren’t technically late-night hosts, but they’re chummy enough with the gang for a mention. After O’Brien, Stewart, and Colbert engaged in a very public, and very fake, feud during the writer’s strike, the two Comedy Central stars decided to pop into the crowd at Conan’s show on TBS. Stewart’s presence causes a stir, but it’s Colbert who really gets the audience cranked up. Colbert may be the only host with a fan base as loyal and ardent as O’Brien’s has proven to be.

3. David Letterman on The Tonight Show with Johnny Carson, 1991.

Jay Leno took the Tonight Show reins from Johnny Carson in 1992, but not before rival host David Letterman had his say. Letterman appeared on Carson’s beloved program to talk about the passing of the torch and to express his bemusement. Carson sums up the situation best when he asks wryly, “Just how pissed off are you?” It’s wonderful, though, to see the effortless rapport the two men have – by this time they had known each other for a decade – as they eagerly, and hilariously, poke fun at each other.

2. Conan O’Brien on The Late Show with David Letterman, 1996

Conan’s first appearance on Letterman’s new CBS show in 1994 was a bit shoddy, but when he returned two years later he was much more confident – and much, much funnier. He unveils a ridiculously short Super Bowl promo spot and talks about getting over stage fright: “I’m drunk now, Dave.” It’s a glimpse of the deadpan, self-assured delivery that would carry NBC’s Late Night with Conan O’Brien for 16 years.

1. Jimmy Kimmel on The Jay Leno Show, 2010

Jay Leno drew the ire of most of the late-night community when he booted Conan O’Brien from the Tonight Show post. So when he invited Jimmy Kimmel to appear via satellite during the last days of The Jay Leno Show, Kimmel used it as his own personal roast. It’s obvious that Leno regrets this decision early in the “10 at 10″ segment but he simply has to finish, giving Kimmel ample opportunity to repeatedly skewer the host. This is vicious, topical television at its cringe-worthy best.

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