Top 10 Cringiest Curb Your Enthusiasm Moments

This show’s cringe factor largely stems from the fact that Larry David simply can’t keep his thoughts to himself. Out to dinner with his wife Cheryl and a Japanese art dealer named Yoshi, Larry drops a bomb of awkwardness. It all begins when Yoshi mentions that his father was a kamikaze pilot during the war, but survived the attack. As far as Larry is concerned, you can’t call yourself a kamikaze pilot if you’re still alive. To make matters worse, he orders the chicken. This naturally gets under Yoshi’s skin, as well the audience’s. The art dealer’s so distraught that he later attempts suicide, which Larry doesn’t consider that big a deal. After all, no one died. Yikes!

The Holocaust is already a touchy subject to bring up at the dinner table. Throw Larry into the mix and you have a recipe for disaster. After Larry’s father invites a holocaust survivor to Larry and Cheryl’s 10th anniversary dinner, the Rabbi asks if another survivor can come too. What Larry doesn’t realize is that this particular “survivor” was actually a contestant on the reality show. This amounts to a hysterically uncomfortable debate in which the two very different survivors argue what’s worse: being held prisoner in a concentration camp or being stuck on an island littered with First World problems. As the conversation reaches its boiling point, everything blows up in Larry’s face. It’s a miracle HE survived.

Even when he acts with good intentions, Larry David inevitably winds up at the center of controversy. Following the death of Cheryl’s “beloved aunt,” Larry is tasked with writing her obituary. Although Larry’s words are respectful, the newspaper makes a cataclysmic spelling error. Needless to say, Cheryl and her family aren’t at all pleased, pinning the blame on Larry. Watching Cheryl’s mother break down in tears only adds to the tension, as well as the hilarity. Larry is consequently kicked out of his own house. This is why the letters “A” and “C” should be kept on opposite spectrums of keyboard... AND why you should never dictate important passages to friends with questionable handwriting.

Upon meeting Richard Lewis’ African American doctor, Larry cracks a joke about affirmative action. For those that don’t know, this is when a disadvantaged group of people is given a leg up. Although Larry was just trying to be funny, the doctor understandably is NOT amused. As cringe worthy as this encounter might be, the tension is kicked up to eleven when Larry is forced to relive the incident in a room full of black people. Thankfully, everyone eventually laughs it off, but just when you let your guard down as a viewer, a black woman enters the room and labels Larry a racist for not hiring her. This is the cringe that keeps on giving.

How can “Curb Your Enthusiasm” possibly top the affirmative action comment? How about with the single most offensive name you can call a black person? In a bathroom stall, Larry overhears a disgruntled man spouting a racial slur. Although Larry has made his fair share of jokes at the expense of African Americans, even he finds the N-word appalling. Larry is so shocked that he relays the incident to his date. A black doctor passes by at the exact wrong time, however, resulting in a freak out of epically awkward proportions. Everyone in the room is left with their jaws hanging wide open, and the same can be said about the audience.

Larry is taken aback upon realizing that his latest love interest is in a wheelchair, but gives the relationship a chance regardless. After losing his BlackBerry, Larry can’t get back in touch with the woman he has labelled “Denise Handicap.” Trading in one paraplegic date for another, Larry attends a violin recital with a woman he refers to as “Wendy Wheelchair.” As fate would have it, Denise is also present, prompting Larry to stash Wendy in a closet. Both women inevitably confront him with some help from Rosie O’Donnell, who looks like she’s ready to put Larry in a wheelchair. In typical “Curb Your Enthusiasm” fashion, this awkward moment brilliantly brings matters full circle.

In what’s been called the show’s best episode, Larry finds himself torn between his people and the chicken he loves so much. Shortly after accepting his role as a social assassin, Larry pushes Marty Funkhouser’s buttons like never before by trying to snatch his yarmulke. Larry receives applause from the Palestinian restaurant, as well as a woman’s phone number. The cringe factor literally climaxes as the two later engage in anti-Semitic intercourse while the Funk Man eavesdrops. The words that come out of Shara’s mouth are so wrong, but the moment feels so right to Larry. It just goes to show that nothing is sacred to him… except for maybe sex and chicken.

After giving a little girl’s doll a very unbecoming haircut, Larry jumps over several hurdles to set things right. The ordeal leaves Larry with an itchy penis, which he tries to remedy by placing a water bottle in his crotch. This turns out to be a colossal mistake, as the little girl enters the restroom and gives Larry a hug for fixing her doll. Feeling something erect in Larry’s trousers, the traumatized girl darts out of the bathroom and delivers one of the show’s most uproarious lines. Rather than facing his audience, our protagonist stages a bathroom breakout through the window. Maybe this is why Larry and Cheryl never had kids.

If you thought our last entry had “stranger danger” written all over it, just wait until for this cringe fest. Larry is caught off-guard when a mother casually tells him that there’s a rash on her daughter’s vagina, but doesn’t use that word. It isn’t long until Larry also starts nonchalantly mentioning the rash in front of others, using the same shocking word choice. To make matters even more suggestive, Larry forms a friendship with the nine-year-old via text messages. We can certainly understand why Larry’s doctor jumps to the wrong conclusion and calls the cops on him. Larry’s poor choice of words might land him in hot water, but the results are comedic gold.

Before we get to our top pick, here are a few honorable mentions:
- Stealing Flowers from Roadside Memorial
“The Ida Funkhouser Roadside Memorial”

- Michael Richards Yells at Leon
“The Table Read”

- The Missing Baseball
“The Ski Lift”

“Curb Your Enthusiasm” has set the bar pretty high for dark comedy, but our top spot had to go to this moment, which manages to offend multiple groups of people in just a couple of minutes. In a doctor’s waiting room, a bald man bombards Larry with a slew of hate-filled slurs. As if that’s not uncomfortable enough, Larry later returns to the doctor’s office and spots another bald man from behind. Full of bottled-up anger, Larry lets the skinhead have it. The problem is that he’s not a skinhead, but a chemo patient. Adding injury to insult, Leon makes the same incorrect assumption and accosts the man immediately afterwards. It’s classic comedy at its cringiest.