A look back at some of ‘Curb Your Enthusiasm’s’ top cringe moments

“Curb Your Enthusiasm” served up a symphony of social disaster over the course of 12 seasons and almost 24 years on HBO, wringing cackles and cringes from the misadventures of the serially inappropriate Larry David. David, playing a version of himself who could get away with saying and doing the kinds of things that would earn most people a punch in the nose, delighted in pushing past the conventional limits of TV comedy acceptance, at least in the show’s early years, when shock was more possible than it is today.

In the wake of “Curb’s” April swan song, which found Larry in court defending himself against an era’s worth of aggrieved parties, we thought it might be a pretty, pretty, pretty good idea to tally some of the greatest moments and episodes of “Curb” awkwardness. To get an insider perspective, we asked three writers on the series — Carol Leifer, Steve Leff and Nathaniel Stein — for their favorite encounters and scenarios of embarrassment and infamy.

Carol Leifer

Leifer was tuned in to the David sensibility even before “Curb,” having worked as a writer and story editor on “Seinfeld” (created by David and Jerry Seinfeld). The first “Curb” episode she mentions is “The Doll” (Season 2, Episode 7), in which Larry gives a little girl’s doll a haircut, deals with a restroom that has no lock on the door and has to chug water nonstop under doctor’s orders. Like all “Curb” episodes, this one culminates in a convergence of plotlines, as the girl hugs Larry, who, with no pockets, has stuck a water bottle down his pants. Emotional trauma ensues.

“As a viewer watching the show, I was definitely thinking, ‘Oh, OK, we’re in very interesting territory now,’” Leifer says. “It is so incredibly edgy and wrong, but Larry gets away with it. If you pitch that in a room now, people would be like, ‘There’s no way you can do that.’ And it’s all turned into laughs, which is the genius of the show and the genius also of him as a character and an actor.”

Leifer recalls the line that David would use to reject story ideas he didn’t like for “Seinfeld”: “I could see that on another show.” “Curb” was teeming with ideas you couldn’t see on another show.

Steve Leff

Some of Leff’s favorite “Curb” moments revolve around race, particularly Larry’s talent for saying the exact wrong thing to and around Black people. This was evident even before J.B. Smoove joined the regular cast as Hurricane Edna refugee Leon Black in 2007 and stuck around as a fan favorite through the series’ conclusion this year.

Leff points to “Affirmative Action” (Season 1, Episode 9) as a prime example. Larry meets Richard Lewis at the beach, where they encounter Dr. Grambs (Gregg Daniel), who is Black, out for a jog. When Richard introduces the doctor as his dermatologist, Larry responds with a pointedly unfunny affirmative action joke. Grambs is appropriately offended. Later in the same episode, Larry encounters a Black line producer whom he didn’t hire for his movie, “Sour Grapes”; she accuses him of racism. Of course, these two storylines dovetail by episode’s end.

“He meant no ill will toward the doctor,” Leff says. “Obviously, it did not go over well. But he didn’t say it behind his back. Larry’s not a racist. He’s just sometimes an idiot. Like he tells Richard, ‘Sometimes I say dumb stuff around Black people.’ He owns that.”

Leff sees the affirmative action incident as one of many examples of Larry making bad choices, rather than experiencing bad luck: “He chooses to make this joke. In Larry’s own words, ‘I was just trying to be affable.’ For some reason, he thought that was a friendly way to ingratiate himself to this African American man. That’s his own doing.”

Nathaniel Stein

Stein was a “Curb” superfan before he joined the series as a writer. “The only reason I’m able to contribute anything to ‘Curb’ is because I have seen the episodes 50 times each,” he says.

One of Stein’s favorites is “Chet’s Shirt” (Season 3, Episode 1), which features another of Larry’s great talents: lying. Here Larry has begged off a social engagement with his dentist, Dr. Blore (David Pasquesi), by lying about an out-of-town trip. As bad luck would have it, Larry runs into another of Blore’s patients, Burt Bondy (Chris Barnes), at a clothing store when he’s supposed to be out of town. As further bad luck would have it, Larry is then whacked in the mouth (perhaps on purpose) by Ted Danson’s daughter, who was swinging at a birthday party piñata.

Bondy has told Dr. Blore that he ran into Larry, who was very much in town. Larry needs emergency dental work. You think you can see where this is going. And yet the results are still unexpected and hilarious.

Stein has become something of a student of Larry’s lying. “So much of it is about getting caught lying,” he says. “You never know exactly how it’s going to happen, and it often happens in a way that you don’t think it’s going to happen. However, there are also times when he doesn’t get caught. Sometimes he lies for absolutely no reason and gets away with it. And I love that.”

Larry is the lying, socially inept, passively offensive curmudgeon you wouldn’t be able to stand in real life. And we will miss him dearly.