Rejoice, Curb Your Enthusiasm fans: your seemingly unending nightmare is almost over. After a six-year hiatus, the beloved comedy is finally returning to television, premiering October 1 on HBO. And that’s “prettay, prettay, prettay good” news.

The genius of Curb Your Enthusiasm lies with its creator Larry David, who has managed to one-up his legendary ’90s sitcom Seinfeld (which he co-created with its namesake) in terms of social awkwardness among frenemies, family and business associates – not to mention its coarser content.

Larry’s appeal to audiences lies in just how unappealing he is. Sometimes he’s an intentional jerk, unafraid of defying social niceties if he feels someone is asking too much of him, or annoying him with some minor irritant. Other times he deliberately tries to avoid controversy, but somehow manages to cause it by accident by just being who he is. Over 8 seasons, Curb has continually topped itself in the type of cringeworthy social exchanges Larry finds himself trapped in, and the desperate (and futile) means by which he tries to dig himself out of them.

So in honor of what fresh horrors season 9 will bring for our beloved, yet horrible protagonist/antagonist, here are the 15 worst things Larry David has ever done on Curb…so far.

15. Assumes a Black Man in a Suit is a Car Park Attendant (“The Surrogate”)

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“The Surrogate” is one of several Curb episodes that deals with racist stereotypes and how Larry always seems to always stick his foot in his mouth in such situations, often while trying to do the opposite. In this episode, he gets in hot water when he assumes that a black man is a valet while leaving a restaurant.

Needless to say this, doesn’t go unanswered, with the offended party replying  “Yeah, I’m not the valet. It is possible for black people to have other jobs. You f***** up!” before leaving in a huff. This embarrassing moment is memorialized when his friend Wanda Sykes witnesses the entire affair.

Larry mounts a defense: “He had on a white shirt, a red tie and a vest, he’s standing by the valet sign! It’s an honest mistake!” Wanda gives him the stinkeye, replying “Oh, oh yeah, that’s honest! Anytime I see a black man in a tie and a suit I say: “‘Hey, you must park cars for a living!'”

14. Steals Flowers Off a Grave  (“Ida Funkhouser Roadside Memorial”)

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Some of Larry’s worst moments come when he tries to atone for other offenses, resulting in a chain reaction of awfulness that unravels in a strange sort of balletic grace. And “The Ida Funkhouser Roadhouse Memorial” is a true case in point.

After offending the headmistress of a school that Loretta Black hoped to get her child into, Larry tries to make amends. His solution? To swipe the flowers from the grave off his friend Marty Funkhouser’s (Bob Einstein) recently deceased mother Ida.

To make matters worse, Larry goes back to steal more flowers off an additional memorial (also for Ida) to make amends to both Loretta and her mother. Eventually, Marty discovers this offense, yet he somehow remains pals with Larry, a recurring trope on the show. How does he hang on to these friends??

13. Accuses Ex-Wife of Having a Threesome (“Officer Krupke”)

Curb Your Enthusiasm Cheryl and Larry Curb Your Enthusiasm: 15 Worst Things Larry David Has Ever Done

Larry’s wife Cheryl (Cheryl Hines) left him at the end of the show’s 6th season, but he schemed to get her back when he tried casting her in the Seinfeld reunion as Jerry’s love interest. The problem? Jerry wasn’t entirely sold on her audition, and he wants to give another actress, Virginia (played by Elizabeth Shue), a shot.

Cheryl isn’t pleased with this development, which gets more complicated when her competitor tries to rope her into a threesome with her husband. When Larry sees Virginia in a neck brace, he becomes convinced it was an injury caused either by “a car accident or…cunnilingus.”

Needless to say, this lack of trust puts their rekindled romance in jeopardy, so it shouldn’t have been too shocking to see that it never lasted.

While Cheryl is in the clear, his best friend and business manager Jeff (Jeff Garlin) isn’t so lucky, asking Larry to lie and tell his wife/Larry’s arch-enemy, Susie (Susie Essman), that he likes wearing women’s panties after she discovers a pair that isn’t hers in their car.

12. Steals the Head From a Child’s Doll/Accused of Being a Sexual Predator (“The Doll”)

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In “The Doll”, our miserable protagonist attends a party with Seinfeld-alum Julia Louis Dreyfuss. During his stay, a young girl asks if he’ll give her a doll a haircut. He does. It doesn’t go well, with the child throwing a fit after learning that doll hair doesn’t grow back.

In an effort to smooth things over, Jeff recalls that his daughter Sammie has a similar doll, and plots to simply swap out the heads. Things backfire (of course), when she freaks out over her decapitated doll, unleashing his wife’s wrath.

Larry’s attempt to switch out doll heads goes over well with the girl from the party. But after she hugs him appreciatively, she becomes startled by the water bottle he has stuffed in his pants. She runs to her mother screaming “Mommy, mommy. The old man’s in the bathroom, and he’s got something hard in his pants.“ Once again, Larry provokes laughter from a horrifyingly sensitive topic.

11. Gets a Kid Drunk/Steals A Dog (“The Corpse Sniffing Dog”)

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As we’ve stated earlier, Larry’s interactions with children…have not been great. This is painfully clear in the gut-busting episode “The Corpse Sniffing Dog.” In it, Larry tries to do Jeff a solid by convincing his daughter Sammie to find a new home for their German Shepherd, Oscar. It turns out that Jeff is deathly allergic to the dog, who was acquired during his separation from Susie.

But things go haywire after Sammie mistakes Larry’s glass of wine for grape juice. Soon, Susie accuses Larry of getting her daughter drunk to steal their dog. But by the time she confronts him, Larry has given Oscar a new home, as an apology gift to a friend he had previously offended.

When Susie demands he return Oscar (“You sicko…get me the f***ing dog!”), Larry must steal Oscar yet again, prying him from his new family that has already become deeply attached.

10. Picks Up a Prostitute to Use the HOV Lane (“The Carpool Lane”)

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After scoring some illegally obtained medical marijuana to help with his Dad’s glaucoma, Larry takes off for a sold-out Dodgers game. After getting snarled in L.A. traffic, he does the only thing that makes sense…to him. He picks up a hooker named Monena so that he can dodge gridlock by using the carpool lane to make it to the game in time.

The car ride between the odd couple proves educational for our beloved curmudgeon, where he learns the difference between good and bad weed, and the trade secrets of the sex worker. The two hit it off so well that he invites Monena to the game, and afterwards, they visit with his father. Everyone winds up getting high, ending with Larry having a paranoid freakout in the bathroom.

9. Uses his Mother’s Death to Get Out of Social Obligations (“The Special Section”)

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As we saw earlier, Larry hasn’t much reverence for the dead, and in “The Special Section”, we learn that his own mother is no exception. After returning from a film shoot, Larry learns that his mother has passed. Weeks ago. His father explains that she never wanted to bother him while he was working, and he thought that applied to her dying as well.

Eventually, he learns she’s buried in “the special section“of a Jewish cemetery, relegated for sinners. In this case, it’s a strange and minor offense, because, as he learns for the first time, “My mother has a tattoo on her ass?”

Larry uses the sad event to selfish ends, using it to get out of multiple obligations and to avoid conversations with people he can’t stand, showing there is never any event too sacred or beyond reproach for him to use to avoid social interactions.

8. Offends The Disabled (“Denise Handicapped”)

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After divorcing his wife, Larry tries to re-enter the dating scene, and it goes just about as poorly as you’d expect. The episode “Denise Handicapped” is a painful case-in-point, which sees our misanthropic anti-hero began a relationship with Denise, a woman he agrees to go out on a date with before learning that she is wheelchair-bound.

Despite his initial superficial misgivings (and hers: she doesn’t like dating bald men), the two begin a relationship, and he exploits the politically correct benefits of dating someone with a disability, using it to gain access to a private concert.

If this wasn’t bad enough, Denise becomes (rightfully) appalled when she discovers she’s listed as “Denise Handicapped” in his Blackberry contacts, and they stop seeing each other. Later, he hits it off with Wendy, another woman in a wheelchair, who becomes equally offended when he nicknames her “Wendy Wheelchair,” leading to a hilarious confrontation with both women.

7. Shows Cultural Insensitivity to a Chinese Baby  (“Denise Handicapped”)

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Remember how we mentioned Larry exploited sympathy points to gain access to a private concert in the episode “Denise Handicapped”? Well, it was to smooth over this unpleasant exchange.

Not content with merely insulting his date, Larry doubles down by offending the adoptive parents of a Chinese baby girl. After an initial innocent exchange inquiring about their daughter Chelsea, he awkwardly asks if she’s shown “a proclivity for chopsticks.”

Unsurprisingly, this doesn’t go well, with the father retorting, “Do you think she is also a kung-fu master?!?” He makes matters worse by wondering if they’ve ever wondered if the biological parents were mentally ill and they might have a schizophrenic on their hands who could stab them in their sleep. He should have quit while he was ahead.

6. Says “The N Word”

Leon and Larry Curb Curb Your Enthusiasm: 15 Worst Things Larry David Has Ever Done

Curb once again explores Larry’s awkward discussions on race, which rears its ugly head while he hosts the Black family in his home, who were displaced after Hurricane Katrina. Larry gets read the riot act after they overhear a conversation between him and Jeff, where he was quoting a racist he met. But they believe he said the N word on his own accord, and things spiral from there.

Jeff also gets in trouble, because his surgeon (who happens to be black) also overhears the conversation and shaves his head during a procedure (done out of spite, not medical necessity). This series of misunderstandings becomes exacerbated when Jeff sues the doctor for abuse. Larry is called to later testify in court and explain to the judge how the conversation occurred, but once he witnesses a black juror, he freezes, unable to say the word that caused the trouble in the first place.

5. Urinates on a Painting of Jesus (“The Bare Midriff”)

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In “The Bare Midriff”, Larry goes to take a leak, leaving behind some accidental spray on a painting of Christ. But when Larry and Jerry Seinfeld‘s mutual assistant Maureen (Gillian Bell) sees it later, she believes it’s actually Jesus crying, and a sign from God for her to change her ways.

She decides to quit her job and travel the world, sharing what she believes is a true miracle with others seeking inspiration in their life. Given that Jerry and Larry were unimpressed with her service (and distracted by her shirt revealing her stomach), they aren’t overly distraught, but her career change sends her depressed mother into a suicidal state.

Larry and Maureen rescue her from jumping off a building just in time, but not before Larry almost accidentally falls to his own death (saved only by grasping… Maureen’s bare belly).

4. Broke up with his girlfriend after she was diagnosed with cancer (“Vehicular Fellatio”)

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For anyone hoping that Larry and Loretta Black (Vivica A. Fox) were going to run off into the sunset after the season 6 finale, the season 7 premiere “Vehicular Fellatio” killed those hopes for good. In it, we learn Loretta has been diagnosed with cancer. The always superficial Larry was never going to handle this news well, but Loretta doesn’t help things with her brutal guilt-tripping technique that injects the topic of cancer into every conversation.

Larry tries to find a way out, referring Loretta to an oncologist who encourages patients to end “toxic relationships,” while acting more obnoxious than usual in hopes that it will inspire her to leave him. In the end it doesn’t–the final nail for Loretta is when she thinks she sees another woman performing oral sex on Larry in his car. This was actually a misunderstanding, but in the world of Curb, everything appears to be a case of misunderstanding. This was just the rare case that gave Larry the desired result.

3. Eats at an Anti-Semitic Chicken Restaurant/Has Sex With Its Owner  (“Palestinian Chicken”)

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Only the mind of Larry David could mine the Israeli-Palestinian conflict for laughs–and base it around food. When Larry discovers the hottest new restaurant in town is owned by a Palestinian family who displays anti-Jewish propaganda, he says screw it and tries it out, with Jeff in tow.

The two joke that it would be the perfect place for Jewish men to bring their affairs on dates, as they’d be highly unlikely to run into any folks they knew there. Larry is assailed by his friend Marty Funkhouser (who had recently coverted to Judaism), who claims he’s a traitor to his Jewish heritage by patronizing the eatery, but Larry can’t resist the food…or the attractive woman who works there.

Eventually, the two engage in a sexual relationship, with the woman engaging in some particularly racist dirty talk: “I’m going to going to f*** the Jew out of you. You want to f*** me like Israel f**** my country?

2. Writes an Offensive Obituary (“Beloved Aunt”)

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While many of Larry’s worst moments happen deliberately, sometimes, he’s just subject to bad luck. Take, for instance, the time he tried to write a respectful obituary for his wife Cheryl’s deceased aunt.

What should have read as a short-but-sweet tribute (beginning with the words “Beloved Aunt“) gets destroyed by a fatal typo: “Aunt” is misspelled with a “C” instead of an “A”. Yep, Cheryl’s favorite aunt gets immortalized in the L.A. times as the C-word. Yeesh.

As expected, no one takes Larry’s apology to heart, and he’s on the outs with his wife and her in-laws. Things get even worse after Larry imparts poor relationship advice to the boyfriend of Cheryl’s sister, who breaks up with her the day of the funeral. And did we forget to mention that Larry accidentally feels up the mother of his best friend in the same episode? No extended family member escapes Larry’s presence unscathed.

1. Accuses Michael J. Fox of Using Parkinson’s Disease As An Excuse to Harass Him (“Larry vs. Michael J. Fox”)

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Yep. He went there. In the season 8 finale (and the last series episode until this year), Larry gets in a feud with Michael J. Fox, who happens to live directly above his New York City apartment. The two first run into each other at a restaurant, with Larry wondering if Fox’s arm shaking is from Parkinson’s Disease, or if it’s a disapproving movement directed at Larry himself.

The rest of the episode sees Larry obsessed with discovering if Fox is using his symptoms as an excuse to humiliate him (such as handing him a can of soda that explodes all over him, or saying he needs special shoes for foot cramps, the noise of which keeps Larry up all night). This leads to the classic catchphrase “Pissed…or Parkinson’s?”

Larry’s feud with Fox reaches his zenith at the conclusion of the episode, with mayor Michael Bloomberg kicking him out of the city after he thinks he saw Larry mocking Fox while giving a speech. Larry always knows how to make a grand exit.

Well that wraps up our list of Larry David’s worst moments! Which ones would you add to the list? Tell us in the comments.

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