Larry David’s 12 Most Unforgettably Awkward Moments in 'Curb Your Enthusiasm'

Larry David returns for one final season of Curb Your Enthusiasm on Sunday, Feb. 4, on HBO. To say he will be sorely missed is an understatement. Between his 12 seasons on Curb, and his seven seasons as the head writer of Seinfeld (which he co-created with Jerry Seinfeld), David has molded the American comedy landscape in his own neurotic image.

Who knew that the mundane could be so funny? That one could mine pitch-black comedy out of social faux pas for three decades? David knew. And our lives, our ability to laugh at ourselves and the absurdities of modern life, are better for it.

In recognition of Curb's 12 seasons, we're reminiscing on the 12 most unforgettably awkward moments from the show's run—the moments where Larry's lack of filter and lack of social awareness coalesced, and things got bad. Prettay, prettay, prettay bad.

Episode: "Thor" (S02, E02)

Cheryl is a fantastic woman for Larry, because she knows how to corner him into contradicting himself. She asks a general question, and then she asks a more specific, incriminating question, giving him just enough rope to hang himself. An awkward greeting becomes a referendum on Larry's ass fetish, and that's Curb at its finest.

Episode: "The Shrimp Incident" (S02, E04)

The c-word is a vulgar epithet in every English-speaking country. But in America, the c-word is nearly forbidden, to a point where you're a misogynist if you use it regardless of context. Combine that with Larry's line delivery—his loud, over-the-top forceful way of saying anything—and we have a completely ruined poker night.

Episode: "Affirmative Action" (S01, E09)

"I tend to say stupid things to Black people sometimes," laments Larry at the end of this clip. How's that for understatement of the year? Within 30 seconds of meeting Richard's dermatologist, he makes an ill-advised crack about affirmative action. The most awkward part of the ensuing exchange is Richard's attempt to defend his friend: "He's a liberal!" By the end of the episode, Larry manages to make this situation even worse. But the awkward, pregnant pauses of this first interaction are the most cringe-inducing in the episode.

Episode: "Larry vs. Michael J. Fox" (S08, E10)

There's something both incredibly daring and oddly empathetic about this feud, in which Larry believes Michael J. Fox is playing up his Parkinson's. For decades, we've watched one of our most beloved actors suffer from a cruel, debilitating condition. To make jokes about this—and to have Fox be complicit in them—depicts Fox and other sufferers in a way that they typically aren't afforded. To be spoken to as just another person, rather than as a martyr in hushed tones, must be humanizing, and might come as a relief.

Episode: "The Ida Funkhouser Roadside Memorial" (S06, E03)

Larry takes an atheist's approach when he reappropriates the flowers from Marty's mom's memorial as gifts to Cheryl and Loretta. One of Larry's funniest qualities whenever he gets caught in scenarios like this is that he tries to defend himself until the point that people start screaming. And his justification in this situation is one for the books. "How many flowers does she need?"

Episode: "The Divorce" (S08, E01)

Larry helps a middle schooler insert a tampon for the first time. My God. Just writing that sentence makes me want to curl up into a ball. The little details stand out in this one, especially when Larry uses the crease of his armpit to create a faux vagina. But the fact that he's successful at teaching the girl is surprisingly wholesome. Larry doesn't get very many victories, and this is about the best he can do.

Episode: "The Lefty Call" (S06, E04)

After being hyped up by Leon to stand up for himself ("You get in that ass, Larry!"), Larry decides to give a skinhead a talking to. Unfortunately for him, it's actually a cancer patient undergoing chemo. It's an honest mistake though, right? Happens to the best of us.

Episode: "The Surrogate" (S04, E07)

I love two things about this scene. The first is that regardless of the truth, Larry is trapped in this situation by happenstance. Even if he didn't mean to be racist, he can't seriously expect the man he mistook for the valet to know that. So when Wanda Sykes comes in at the end and takes the piss out of him, it's perfect—not only because Sykes is a perfect comedic foil for Larry, but also because we get the feeling that she relishes his awkwardness and takes great joy in busting his chops. It's as if she's been waiting for the perfect moment to lay into him, and now that it's finally here, she's going to savor it.

Episode: "Car Periscope" (S08, E08)

Oh man, this clip has it all. The social awkwardness. The loaded expectations around body type. The gender dynamics. The escalating anger that climaxes with an off-screen ass whopping. And the very last shot, of Larry tossing popcorn at the woman like she's an animal, brings every unspoken implication to the forefront.

Episode: "The Table Read" (S07, E09)

What makes this hilarious is that at first, even Larry is shocked by how the mother discusses her daughter in such crude terms. But instead of viewing it as an aberration, he takes it the other way and sees it as permission for him to do the same thing. It's not the first time that Larry's been mistaken for a pedophile. But it's definitely one of the most appalling.

Episode: "The N Word" (S06, E08)

In the course of relaying a story about a racist, Larry uses the n-word within earshot of a Black person. And he does this not once, but twice—first, in front of the Black doctor who's performing Jeff's surgery, and second, in front of Loretta, who promptly calls over Auntie Rae and Leon to pile on. The two best details about this exchange: Larry's visible horror at Leon's involvement ("Ohhhh nooooo!") and Leon's reaction, which is more about sowing additional chaos than getting an explanation.

Episode: "The Doll" (S02, E07)

Through a series of truly inauspicious narrative twists, Larry winds up in a women's bathroom, hugging a little girl, with a water bottle stuffed down the front of his pants. You could live three lives and never be in as much trouble as this, and Larry knows it. Usually, no matter how wrong he is, Larry attempts to explain himself, even over the yelling of furious people. But this time, he just tries to escape out the window. He knows there's nothing he could possibly say to make this better.