Seinfeld differentiated itself from other ‘90s sitcoms by being the one with the darkest, most daring sense of humor. Years later, series co-creator Larry David applied this same sensibility to his HBO sitcom, Curb Your Enthusiasm, except this time, he threw out the rulebook.

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Every scene of the show has entirely improvised dialogue, so the actors can really lean into the cringe. When David is writing a story outline for Curb, the plot developments themselves have to be funny, because there’s no scripted dialogue to carry a boring, uneventful plot along. That doesn't mean it doesn't get dark though. Here are Curb Your Enthusiasm’s 10 darkest storylines, ranked.

Larry accidentally prints the C-word in a family obituary (Beloved Aunt, Season 1)

When Cheryl’s aunt dies, Larry makes an innocent-enough offer. He has a friend who works at a newspaper, so he tells Cheryl’s family that he’ll handle the obituary.

It’s actually pretty kind, by Larry’s standards. Unfortunately, between Larry dictating the obit to Jeff and Jeff sending it off to the presses, a typo occurred, and “beloved aunt” was misprinted as “beloved c**t.”

Larry David came up with the most shocking comedic use for the fact that “aunt” and the C-word are just one letter apart. Cheryl’s family is mortified when the paper is delivered, and Larry is promptly kicked out of his own house.

Larry stages a mugging to trick Cheryl’s therapist (The Therapists, Season 6)

Cheryl decides to leave Larry in the middle of Curb’s sixth season. They both begin seeing therapists in order to get through the breakup. Because Cheryl has painted a negative portrait of Larry for her therapist, the therapist’s recommendations are all based on getting Larry out of her life.

As long as that therapist hates Larry, he has no chance of winning her back. So, he gets his own therapist – played by guest star Steve Coogan – to pretend to mug Cheryl’s therapist, allowing Larry to gallantly jump in and stop him, thus looking like a hero in Cheryl’s therapist’s eyes. The web of deceit and emotional manipulation is all very disconcerting.

Susie is attacked and thrown from an upstairs window by her new nanny (The Nanny from Hell, Season 3)

Early in the season 3 episode “The Nanny from Hell,” Susie finds out she’s pregnant but warns Jeff that it’s bad luck to tell people in the first three months when he tells Larry. When Larry accidentally gets his friend’s nanny fired, she feels entitled to a job from him. So, he promises to introduce her to Susie.

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As long as Susie’s pregnant, she’ll need a new nanny. However, after Susie hires her, the nanny goes crazy and attacks her and throws her from an upstairs window. The only reason Susie’s still alive is that Larry brought over a bunch of cake for Jeff that she tossed next to the dumpster, which cushioned her fall.

Larry adopts a racist dog (The Bowtie, Season 5)

In the season 5 episode “The Bowtie,” Larry adopts a dog named Sheriff from a shelter. The dog is perfectly pleasant and cuddly when he’s around white people, but whenever he’s near a black person, he starts barking and jumping at them.

Larry insists that he didn’t train the dog to be a racist, but worries that one of Sheriff’s previous owners did. When Larry and Cheryl’s friend Wanda Sykes comes over, she tells them they’ve “got a Klan dog,” and when Larry tells her that the dog’s name is Sheriff, Wanda quips, “Sheriff? That’s a perfect name for a racist dog!”

Larry attends a group therapy session for incest survivors (The Group, Season 1)

In the season 1 finale “The Group,” Larry bumps into an ex-girlfriend. She’s an incest survivor and Larry is the only person she ever told about it, so she wants him to join her in a group therapy session for emotional support.

So, he goes along and listens to everybody in the circle opening up about their trauma. And then the burden falls upon Larry to open up. He tries to get out of speaking, but he’s encouraged to talk, so he makes up a story about an uncle who’s coming to visit, using a fake name. This comes back to bite him when someone from the group encounters Larry and the uncle is with him.

A Revolutionary War re-enactment triggers an Afghanistan war veteran’s PTSD (Thank You for Your Service, Season 9)

In the season 9 episode “Thank You for Your Service,” everybody thanked Sammie’s new fiancé, Victor – a veteran of the war in Afghanistan – for serving his country, except for Larry.

Larry refused to say, “Thank you for your service,” and as a Seinfeld fan, Victor was pretty disappointed. So, Larry tried to make it up to him by bringing him to a Revolutionary War re-enactment.

At first, they were having a great time, but then a toll booth operator that Larry offended started using real cannonballs, which triggered Victor’s PTSD. This led him to attack some valets that he mistook for enemy soldiers.

Larry steals flowers from a memorial (The Ida Funkhouser Roadside Memorial, Season 6)

Marty Funkhouser refers to himself as an “orphan” in the season 6 episode “The Ida Funkhouser Roadside Memorial,” because both of his parents have died. Larry insists that a grown man can’t be an orphan, but that’s how Funkhouser feels.

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Funkhouser’s mother was hit by a car in her wheelchair, and at the spot where it happened, some mourners and well-wishers have left bouquets of flowers to show their respect. When Larry needs some flowers to make up with a few people he’s offended, he doesn’t bother to go to a florist, and instead just steals a bunch from the memorial site.

Larry and Richard drug a Christian Scientist (The Benadryl Brownie, Season 3)

Curb Your Enthusiasm – The Benadryl Brownie

Richard Lewis starts dating a Christian Scientist (someone whose religious beliefs condemn medicine and instead advise waiting for God to miraculously heal them) in the season 3 episode “The Benadryl Brownie.”

After a brownie containing nuts triggers an allergic reaction, her face puffs up (although the episode doesn’t actually show it, to leave it to the audience’s imagination). Lewis wants her to look good for the Emmy Awards ceremony he’s taking her to, and he knows that a Benadryl will clear up the reaction. So, he and Larry try to sneak the Benadryl into her system via another, nut-free brownie.

Larry invites a sex offender to Passover (The Seder, Season 5)

Rob Corddry guest-starred in Curb’s season 5 episode “The Seder,” which chronicled Larry and Cheryl’s preparations for Passover. Larry was mulling over who to invite and gentile Cheryl was getting ready to cook for her first Jewish holiday. Meanwhile, a sex offender moved into the neighborhood, alarming everybody.

Larry met the sex offender and immediately became endeared to him, because he helped him with his grocery shopping, told him he was a huge fan of Seinfeld, and gave him a useful golf tip. So, he got a pass from Larry. But all of Larry’s other guests had a harder time coming to appreciate the guy’s company.

A Survivor contestant claims he suffered more than a Holocaust survivor (The Survivor, Season 4)

Larry David found a goldmine of pitch-black comedy when he paired two meanings of the word “survivor” – one, meaning a survivor of the atrocities of the Holocaust, and the other, meaning a contestant on the reality show Survivor.

In the Curb episode “The Survivor,” Larry’s father invites his Holocaust survivor friend over for dinner, so Larry asks his rabbi to invite his own “survivor” friend over, so they’ll have something to talk about. However, when the rabbi’s friend arrives, everyone’s shocked to discover he’s a Survivor contestant – and he believes he went through worse things than the Holocaust survivor did.

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