Curb Your Enthusiasm’s 10 Most Cringeworthy Moments

It's not easy being Larry David, but it's also not easy watching Larry David


Our Sultan of Shrivel, Our Czar of Can’t-Look-Away, Seinfeld creator Larry David returns with the 10th season of Curb Your Enthusiasm this Sunday. For nine seasons between 2000 and 2017, the man who perfected the weeknight sitcom in the ‘90s upped his own ante, taking harrowing discomfort to Herculean echelons Darren Aronofsky could only dream of. If you thought mother! was gruesome, try watching David explain a poorly landed affirmative-action joke to a dinner party full of black guests. Curb Your Enthusiasm took elements of mumblecore, Neil Hamburger, and postmodern anti-comedy, fusing them with Seinfeld’s borscht-belt humor, with David as its perfect conduit, the hapless, self-destructive schlemiel.

The series would’ve been nothing without its rich nuance, though; David genuinely cares for his once, former, and possibly future wife Cheryl, and they had plenty of tender flirtations even after his worst exercises of judgment. Even his occasionally lecherous manager Jeff Greene and his own foul-mouthed, Larry-hating chainsaw of a wife Susie brought profane slapstick to a household that had identifiable relationship elements if not plausible ones. But we’re not here to celebrate those aspects. We’re here to cringe, sigh, gape, perhaps even scream, at the deeply inadvisable and futile efforts of Larry David, a superhero who can leap from one problem to a much, much bigger one in a single bound. It’s a bird, it’s a plane, it’s … a man who respects wood.

Here are the 10 most jaw-dropping instances where our Bald Asshole turned a bad situation into a world-historical ballet of errors.

10. Saying and then not saying the N-word

From “The N Word”, Season Six, Episode Eight

Only with this show would a white protagonist uttering the N-word rank at only No. 10 on a list like this, and that’s due to a couple key factors. One, only the Trump presidency has been building to a moment like this for a longer time – when your uproarious rated-R comedy series gets to a sixth season, there are only so many ways you can still shock your audience. We’d been expecting this ever since Larry confessed in the very first season, “I tend to say stupid things to black people sometimes,” and taking in a displaced African-American family via Hurricane Katrina called the Blacks for the Season Six arc was basically circling the wagons.

And two, Larry was merely quoting a racist on his cell phone that he overheard in a hospital bathroom. As he repeatedly recounts the use of the most vilified slur in America to various acquaintances, the show, by this time, knows we know a black person is going to walk by at that exact second, which sets up the rest of the dominoes, i.e. hearing the word causes Jeff’s black surgeon to shave the manager’s head under duress and postpone the procedure. So, when the show flips the formula in a hearing at the end, where Larry is required to testify what he heard, the walls are instead closing in because he’s already seen the damage the word has done. In his head-shaking anxiety, you can feel the palpable fear in your own embarrassment for the schmuck.

09. Heckling Jeff and Susie’s daughter Sammi

From “The Hot Towel”, Season Seven, Episode Four

Once again, Curb Your Enthusiasm forces one to rewire the standards to which they order decency. For anyone else, scoffing and booing someone’s kid while they sing would be an unthinkable act of self-mortification. But it’s hardly the most damaging thing Larry’s done to a child, or even this particular child, Jeff and Susie’s daughter Sammi – let’s not forget how he inadvertently got her drunk and stole her dog in Season Three. But this is the rare Curb scene where you’re actually fantasizing about being in Larry’s shoes rather than him pilfering nightmare fuel from your deepest subconscious.

After all, wouldn’t you feel miffed if you bought someone a $300 gift certificate to a swanky restaurant, only to have it be overshadowed by your obnoxious friend trying to pass off their daughter’s bad singing as a “gift from the heart.” As such, each beat, from Larry loudly proclaiming, “This is the worst thing I’ve ever heard in my life,” to him prematurely interrupting the song and shutting it down altogether, and to the shocked faces of partygoers and Susie’s somewhat muted rage, is heart-racing for both better and worse.

Of course, no one’s sympathizing with him when he later screams, “Shut the fuck up!”, at the singing teen once again — in her own home, no less, where Susie really gives him what he deserves: “You heartless piece of shit!” And then, he gets his ass kicked.

08. Hoisting Himself On His Own Petard After Trying to Get Cheryl Back

From “Seinfeld”, Season Seven, Episode 10

The seventh season of Curb is a wet dream for Larry David supernerds because it’s a Seinfeld reunion, and it’s also terribly lenient on our leading man, with partner-in-crime Jerry Seinfeld soaking up some of his foibles with empathy and understanding that he only receives from Jeff, like, half the time. What’s more, his plot to try and get Cheryl back by including her in the reunion episode as George’s girlfriend actually looks like it’s working. In fact, just about everything seems to be going well for him finally, save for a minor scruple involving Mocha Joe (don’t ask) and Julia Louis-Dreyfus’ $500 side table (which he could replace without thinking). But, no one stops Larry quite like himself, and after another series of fortunate bones get tossed his way, including Cheryl showing up at his place, he still manages to lose her. Why? Because she doesn’t “respect wood.”

07. The Double Goodbye

From “Porno Gil”, Season One, Episode Three

Only three episodes in is where Curb found its calling as a spinner of anti-fantasies, putting Larry through the unthinkable: the faux pas of breaking a lamp at the party of someone you barely know and being asked to leave, then forced to return again to that murder scene because you left your expensive watch. Sure, maybe that wouldn’t be so horrifying on its own if it were you, but it’s Larry David, who wouldn’t take off his shoes in the house like the hosts requested, and gets chewed out loudly and thoroughly by the woman sweeping up the glass from the lamp.

Cheryl, of course, leaves him to his own devices, even though she wanted to leave the party most of all – the host, Gil (Bob Odenkirk) is a porn actor fond of recounting tales from on the job. Imagine telling someone you just disrespected twice in their own home, “My feet have a tendency to get a little chilly.” At the same time, the audience can feel that tiny silver of justified smarm in their anti-hero’s soft-spoken bullshit when Gil’s wife Melanie shrieks, “He’s psychotic, get him out of the house!”

06. Discussing a nine-year-old’s “pussy rash”

From “The Table Read”, Season Seven, Episode Nine

Do you honestly think Larry is getting out alive when an adolescent girl with a “rash on her pussy” won’t stop texting him? Jesus, Mary, and Joseph.

05. Forgetting his lines in The Producers

From “Opening Night”, Season Four, Episode 10

It’s not nearly as original as, say, the extended gags about children’s genitalia, but the entire fourth season of Curb was building up to the moment that Larry fucks up onstage in front of an audience as Max Bialystock in The Producers. In fact, it’s kind of the most ordinary public-shaming phobia the show has ever given us. That doesn’t make it any easier to watch a Broadway lead forget his lines onstage in front of all his loved ones and plenty of others. But even then, there’s a chance you’d keep your marbles together better than our Larry, who beckons David Schwimmer to feel his cheek (“It’s like a tushy cheek”) and even gets helped with his lines while inflating his cheek and “popping” it with his hand. It’s a downright live-action Peter Griffin performance. Then again, Mr. David gets the last laugh, foiling a surprise twist by Mel Brooks in a finale that mirrors the central plot of The Producers itself. Still, that minute or two of total uncertainty of what Larry is going to do to get out of this one is as slow-paced and awkward as television ever gets.

04. Being forced to repeat his racist joke

From “Affirmative Action”, Season One, Episode Nine

“You let him work on you even with that whole affirmative action thing?”

And just like that, Curb Your Enthusiasm found its place in the prime-time cosmos. Larry commits a tried-and-true ignorant white-man sin and makes that comment to a complete stranger, Justin, who happens to be an accomplished dermatologist and also a black man. And to what end? “I was being affable!” he insists, while their mutual friend Richard Lewis tries to defuse the situation with an ad-lib that’s kind of haunting in the wake of Trump: “He’s a liberal!” After Justin leaves, understandably, Richard fires back at Larry, “You sounded like Pat Buchanan’s gym partner.”

But that’s merely the beginning of the rollercoaster, as much of “Affirmative Action” is spent in vain, unsuccessfully trying to get Cheryl her prescribed medication for an itch that gets increasingly worse, and you can see where this is going. Of course, before the grand finale, he must prove his underrated devotion to Cheryl by literally digging through a restaurant’s trash for a lost prescription, and flips the bird and makes faces at Richard’s girlfriend at the abbreviated soiree where he promised to try and make nice with her in the first place.

Then there’s the big one: Larry must repeat the tone-deaf comment for an erudite, all-black audience at Justin’s house in order to get Cheryl’s prescription, and his inner tug-of-war is significantly more painful to watch than in “The N Word” later just because TV was much less used to the guy. Seinfeld would always have let George say “Uncle!” by now. But its evil twin showed no mercy, and the episode appropriately includes some of the score from Psycho at one point.

03. “Beloved cunt”

From “Beloved Aunt”, Season One, Episode Eight

So many of Larry’s own downfalls boil down to honest mistakes. Such is the case in this other Season One catastrophe: When Cheryl’s aunt dies and her sister Becky (Kaitlin Olson from It’s Always Sunny in Philadelphia) is dumped, the family gathers around their home to lick their respective wounds. Rather than empathize, Larry stumbles around clueless, concerned more with wrapping presents and the nature of gifts (“Why do i have to get a card? I’m handing her the gift, wouldn’t she know who it’s from”), making you almost beg for his comeuppance.

And then it hits and you feel genuinely guilty: Larry returns to the shiva gathering for Cheryl’s aunt, only to find that his commissioned obituary in the local paper for her has printed the typo “beloved cunt” and the entire party stares daggers through his idiot heart. Even Cheryl asks him to leave, though not before he asks her where he can get a gift wrapped. You know it’s bad when Larry accidentally touching the breast of Jeff’s mother is only the second most-horrifying thing in the episode.

02. Complimenting a child on his large penis

From “The Nanny From Hell”, Season Three, Episode Four

Sometimes it doesn’t have to be a huge blowup or a series of episode-setting traps that makes you scream at your own TV, “What are you thinking?” With Larry David, all it takes is a simple stray nugget of complete brainlessness to completely make you wonder how this guy ever succeeded in life at all: “So I saw your son at the pool yesterday, kid’s got some penis on him.” This is what he utters to his fellow restaurant investor Hugh, who’s rightfully befuddled and enraged at this remark (mind you, his son’s a toddler). And then Larry repeats it, contending: “Hey, it’s a compliment, what’s the big deal?” But it still doesn’t end there, when the brat fights with Larry in a theater and calls him “big nose” and Larry retorts, “Look who’s talking!” Oy fucking vey.

01. Everything having to do with the doll head

From “The Doll”, Season Two, Episode Seven

“The Doll” is one of televised comedy’s master strokes. It’s impossible to outline the Rube Goldberg machine that sets its magic into motion without explaining the entire episode. But there are so many things that must be mentioned, so many people to thank for blessing us with it:

There’s the woman who insists Larry throw out his water before entering a theater, even though she doesn’t work there. There’s the sequence upstairs in the ABC executive’s home that can only be watched through one’s hands, rivaling Larry’s other disturbing stumbles involving children too young to know better (even if the girl in this episode seems like a legit sociopath-in-bloom and her mother a deluded enabler). There’s Larry’s own repeatedly creepy comments about the girl’s doll he inevitably has to replace, and its head that inevitably winds up in his pants, and the rash that inevitably makes it look like he’s masturbating. And finally, there’s that button ending you wouldn’t wish on anyone, even a schmuck like Larry David.

“The Doll” is the quintessential Curb Your Enthusiasm episode, a completely ornate house of cards where if you made a Venn Diagram of time spent laughing versus time spent feeling absolutely horrible, you’d have a circle. I would tell you to pray that you never end up with a doll’s head in your pants, but I doubt you could fail quite as laser-beam perfectly as Larry does here even if you tried.