Letterman’s 10 Most Genuine Moments with His Guests

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In the New Yorker’s 1978 profile of TV icon Johnny Carson, author Kenneth Tynan pinpoints the essential quality of Carson’s genius: contempt. It’s what the paterfamilias talk show host imparted to fellow midwestern David Letterman, rightful heir to the Tonight Show estate. In the early days however, Letterman ran aground. As the 1980s saw the Late Show struggling to find its way, there was no telling what Carson saw in the weatherman-turned-bumbling court jester. Dave’s routine lacked both the deceptive modesty and turnaround wit he’s now able to muster five nights a week, even, and especially when, his guests falter.

Letterman was never a great comedian. Jay Leno was. That their divergent histories produced comic glory for the former and cloying mediocrity for the latter is a matter of understanding their talents and vulnerabilities. Where Leno panders, Letterman prods. Most relevant perhaps, there’s an overriding sincerity present with Letterman, while Leno remains schmaltzy and repressed. And this genuine appreciation of comedic talent was shared by Carson. If you got the invitation for a short sit down after a set on the Tonight Show, you had it made. Though Letterman’s format doesn’t allow him such a gesture, we’ve compiled a list of appearances in which it’s been plain to see who’s gotten the seal of approval from the true king of late night.

Artie Lange — June 6, 2008

Leave it to a comedian to translate the experiences of drug addiction into comedy. Lange’s lucidity makes his comic timing impeccable, because it’s wrought with gut-wrenching honesty. Nothing pleases Dave more than when a guest is aware of their own absurdity, and their chemistry is reminiscent of Buddy Hackett and Carson.

Tina Fey — October 17, 2008

Tina Fey’s doesn’t actually have to be funny to win an audience, but it helps that she usually is. To her credit, Letterman becomes sunnier and almost paternal when she’s on. Sharing a love of schadenfreude, their best moments come at the expense of another.

Russell Brand — March 9, 2009

While the sun is rapidly setting on America’s love affair with Brand, watching his early appearances remind us how we got there in the first place. Brand’s ‘brand’ of Oscar Wildean wit and charm could easily repel Letterman’s modesty, but instead their differences are transcended, and both entertainers seem better for it. Still, it’s no surprise that Brand is a self-professed ‘sex addict’ — the speed and confidence with which he seduces a subject, male or female, leaves one in desperate need of a cold shower.

David Sedaris — July 18, 2008

It’s hard to dislike David Sedaris. If he has an agenda, he cloaks it well, and his discomfort over the publicity charade endears him further. Ruffled by the mundane and yet never untethered, a quiet dignity in the face of highly surmountable odds makes him a Letterman favorite.

Bill Hader — October 2, 2008

Maybe four people in attendance knew who Hader was. Behaving as if he was plucked straight from the audience, the prodigal son plays to his strengths — local yokel lying in wait at a Tropic Thunder reading alongside an overbearing Tom Cruise, or recalling his days as a clumsy PA on the set of a Schwarzenegger movie. He exudes more calm than the manufactured mystique of a bigger name, and Letterman encourages Hader to get even weirder. Killer Seth Rogen impression, by the way. Guarantee that’s gonna become a ‘thing.’

Regis Philbin — January 7, 2011

In the same way that a talk show requires a sidekick or a fall guy, it also needs a bit of drummed up enmity. Dave’s found that in Regis Philbin, who begs for a good natured ribbing — even if that means being forcefed seafood. By the same token, he can be sharp and acerbic, and Letterman’s goading serves to demonstrate that.

Dustin Hoffman — December 22, 2008

“Would you mind very much if I sucked your cock?”

Johnny Carson — May 16, 1985

Carson’s appearance was about handing over the keys to Letterman. Unfolding the Tonight Show desk/ throne and plainly stating it would one day be Letterman’s, the two engage in some light tomfoolery, in the middle of which Carson drops one hell of a metaphor. Who’s your daddy?

Norm Macdonald — May 7, 2009

When Norm’s on, it’s Norm’s show. He’s said in the past that being on The Late Show is tough, because no matter what you say, Letterman’s retorts are 100% funnier than anything you penned backstage. But even if he admits that he’s out to please, you wouldn’t know it by watching him. And he leaves Letterman giggling with the pleasure of a man who might have been faking it until now.

Andy Kaufman — June 24, 1980

It’s the worst of cliches, but Kaufman was ahead of his time. By about thirty, or forty, or a hundred years. He hemmed and hawed, made you boil over with tension, and he wasn’t doing any of this for your amusement. He challenged a very green David Letterman, whose eponymous morning show was on it’s second episode. There were no jokes. You were the joke, and he made fools of us all.

Shona Sanzgiri is writer living in California. His work has appeared in GQ and the SF Weekly.