5 Seriously Awkward Late-Night Moments

5 Sarah Silverman and Bill Burr Get Weird

I Love You, America with Sarah Silverman only lasted one season, but that was enough to give us this eight-minute ode to uneasiness. Silverman gets the conversation off on the wrong foot, introducing Burr as “a brilliant comedian who I love to pieces but who makes me fucking crazy.”

“I thought we got along great,” protests Burr, kicking off a back-and-forth that’s essentially a debate about whether or not the two comics actually like each other. “I feel like with you there’s this person you want me to be,” he tells Silverman, “so you keep telling me that I’m this fucking guy that I’m not.”

The agitated itching continues, with Burr finally proclaiming, “This was one of my favorite interviews!”

But Silverman knows what just happened. “That can’t be true,” she replies.

4 David Letterman Embarrasses Cheryl Tiegs, Then Rubs It In

1980s Dave Letterman made the discomfort of vacuous celebrities into bloodsport. “If the person seems defenseless, you have no business getting in there and hurting their feelings,” he told Newsweek. “But if the person seems to be an incorrigible show-business buffoon then I think they’re a fair target.”

Letterman clearly put Tiegs in the category of “show-business buffoon.” When she showed up on Late Night to hawk her new line of designer clothing — on sale at Sears, of all places — Letterman called bullshit. Incredulous, he asked Tiegs if she actually shopped at Sears. When she said yes, Letterman made it clear that he believed she didn’t. Not exactly a publicist’s dream. When word got out that Tiegs was pissed, Letterman issued the world’s most insincere apology. 

3 Jimmy Fallon Has No Game

Fallon’s over-the-top “reactions” to celebrity stories always feel manufactured. But when Nicole Kidman confessed that she had a crush on Fallon but he was too dumb — or gay — to reciprocate, his mortification felt real. So did Kidman’s disappointed description of what it would be like to date Fallon. 

2 Michael Richards’ Apology

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As mentioned above, Letterman has a way of bringing out the cringe in his guests. For one night, however, Jerry Seinfeld and Michael Richards managed it all by themselves.

For the main event, a clearly shaken Richards (“I’m not doing too good”) appears in what appears to be a hostage video, trying to give his side of the story after a racist tirade at a comedy club. He mumbles his way through an explanation of his “rage” directed at “Afro-Americans,” eliciting giggles from Letterman’s studio audience. 

Enter Seinfeld the Scold. “Stop laughing, it’s not funny,” he chides under his breath, even though the audience believes differently. 

From there, Richards continues to bumble down an awkward path, tying his racist tirade to Black anger around Hurricane Katrina relief efforts (what now?) and equating his fury toward hecklers to conflicts between the United States and other nations. “I’m not a racist,” he protests. “That’s what’s so insane about this.” 

Watch his original outburst and you might disagree.

1 Andy Dick Fondles a Trump

It took until 2022 for the legal system to require Dick to register as a sex offender. But anyone who saw him caress Ivanka Trump’s calf on Jimmy Kimmel Live! in 2007 would be surprised he wasn’t already on the list. 

Kimmel tries to play the sex crime for laughs at first, warning Dick that Donald Trump would kill both of them. But when handsy Dick couldn’t stop his inappropriate groping, Kimmel and security staff had to forcibly haul Dick off-stage. Everyone was laughing but the truth is, Dick is a sociopath.