Over the course of the past 20 years (and 11 seasons), Larry David, or a semi-fictional version of himself, has given fans of Curb Your Enthusiasm some of the most hilarious, uncomfortable, and unforgettable encounters with everyone from Michael J. Fox to Rosie O’Donnell in situations that range from intense to completely over-the-top and asinine. But no matter which way any of these go or how they got started, each and every single one of the dozens upon dozens of these awkward moments are similar to a car wreck in that we can’t look away, no matter how much we try. Here are the best Curb Your Enthusiasm guest stars so far.

By Philip Sledge

In the Curb Your Enthusiasm Season 8 finale Larry David has a series of run-ins with his new upstairs neighbor, Michael J. Fox. Throughout the episode, Larry shushes the Back to the Future star, draws a Hitler mustache on a picture of his father-in-law, and then accuses him of shaking up a soda and purposely stomping on the floor in the middle of the night.

"Larry vs. Michael J. Fox." allows the actor to incorporate his real-life battle with Parkinson’s and use it against Larry David to make him look like an even bigger jerk than he already is. You never really know if Michael is purposely messing with his neighbor or if it’s an honest mistake. There's also one of the best Curb Your Enthusiasm stare-downs. 

The Curb Your Enthusiasm Season 9 finale “Fatwa!” sees the culmination of Larry David’s attempt at producing a Broadway musical. And while there are plenty of great moments throughout the episode, none compare to Larry’s confrontation with Hamilton creator Lin-Manuel Miranda, which ends with the Broadway star challenging him to a paintball duel after Larry verbally runs down his family.

In a callback to Hamilton, Lin-Manuel Miranda aims his gun in the sky just as Larry David trips and fires a shot in his mouth. This is great for many reasons (including Lin-Manuel calling Larry “Aaron Burr”), but the main one here is the fact Larry grinds a decent person down to a level of absurdity they would have never known without him.

Rosie O’Donnell has made multiple guest appearances on Curb Your Enthusiasm, but the most hilarious (and straight-up insane) can be found in the Season 7 episode “Denise Handicap.” The drama starts when Larry David and Rosie have a physical altercation over who’s going to pay for lunch (each of them wants to pick up the tab) that ends with Larry being thrown on the ground.

Later in the episode, Ted Danson comes up to Larry saying he heard Rosie O’Donnell beat him up before calling him a “big f****** sissy.'' The cherry on the top of his confrontational slice of pie comes at the end of the episode when Rosie chases Larry up the stairs after he attempts to flee the two handicapped women he’d been dating at the same time.

Curb Your Enthusiasm Season 7 is largely centered on a Seinfeld reunion including its original cast as well as Larry David’s ex-wife Cheryl (Cheryl Hines), who Larry wants to add in order to win her back. There are multiple great moments involving Jerry Seinfeld, Julia Louis-Dreyfus, Jason Alexander, and Michael Richards, but for the sake of brevity, we’ll just focus on the big picture here. 

Seeing the Seinfeld cast back together again (even if it was in another show) was huge and remains one of the biggest moments of not only Curb Your Enthusiasm but in recent memory on any TV show. For years, it seemed as if something like this could never be pulled off. And until we get an actual Seinfeld reunion like the 2021 Friends HBO Max special, this is the next best thing.

In the Curb Your Enthusiasm Season 2 episode “Shaq,” Larry David accidentally trips Los Angeles Lakers star Shaquille O’Neal when he stretches his legs at his courtside seats. And although the incident leaves Shaq in a hospital bed, Larry finds himself with a string of good luck following the incident. But the universe always has a way of working itself out in the end and Larry’s good fortune fades away as soon as Shaq learns that his injury isn’t all that bad.

This episode is worth a revisit just for the great interactions between Larry David and Shaquille O’Neal, especially the Scattergories scene, even if peanut butter is not a dairy product.

Wanda Sykes has appeared on eight episodes (and counting) of Curb Your Enthusiasm over the years, and each interaction between her and Larry David could very well populate its own “Best Of” list. Ever since the show’s second season, Wanda has been there to be a thorn in Larry’s side and give him hell for being seemingly racist, even when he’s not. The chemistry between the two, which makes for some of the show’s most heated situations, is out of this world, and few people drive Larry up the wall than Wanda (and vice versa).

Ben Stiller appears in the three episodes in Curb Your Enthusiasm Season 4, but the best of the bunch is “Ben’s Birthday Party” which sees Larry David make a fool of himself in classic fashion at the actor’s celebration. Larry first makes Ben mad by not bringing a gift (Ben said no presents), then refuses to sing “Happy Birthday,” and then accidentally stabs him in the eye with a skewer. 

The birthday party would have severe repercussions for Larry David as it leads to Ben Stiller dropping out of the production of The Producers in which they were both set to star. The episode also sees Ben have a series of minor meltdowns brought on by Larry’s grating personality, which makes for some all-time classic moments.

In the Curb Your Enthusiasm Season 2 episode “The Freak Book” Larry David becomes tennis legend John McEnroe’s driver and spends a day with him before taking him to a Paul McCartney concert at the Staples Center. But before the show can begin, Larry and John are kicked out of a pre-party at the arena because of “The Freak Book” and end up yelling at one another like two loons outside the arena. I mean, what’s not to love about these two guys arguing while thousands of passersby watch in shock?

Curb Your Enthusiasm Season 4 focuses on a revival of Mel Brooks’ smash hit The Producers starring Larry David and David Schwimmer (who stepped in for Ben Stiller partway through rehearsals). Throughout the season, Mel is supportive of Larry and does everything he can to make sure his star goes through with the Broadway musical. But then “Opening Night” comes and the big reveal that Mel actually wants the show to fail much like in the story of the musical.

Mel Brooks is in peak form here as a producer who wants to see his production fail, which is ironic considering The Producers is about a show failing so that its organizers can profit. It’s brilliant, and it features one of the final appearances of the Hollywood icon’s late wife Anne Bancroft.

Stephen Colbert only shows up for a moment in the Curb Your Enthusiasm Season 4 finale “Opening Night” as a tourist, but his confrontation with Larry David is just too good to pass up. When Larry is arriving at the theatre for the opening night of The Producers, he is asked to take a picture of a couple out front. When Larry doesn’t take the picture, the man puts a curse on him, which has a pay off when Larry forgets his lines later that night. 

It is great seeing Stephen Colbert here years before he became the host of Late Night and even The Colbert Report, especially with him acting like a seemingly mild-mannered man with one hell of a temper.

Last but not least is Jon Hamm’s appearance on the Curb Your Enthusiasm Season 10 episode “Elizabeth, Margaret, and Larry” in which the former Mad Men star shadows Larry David after being cast as a “Larry-type” character in a movie. Partway through the episode Jon becomes a little too much like Larry and begins to go off the deep end, even saying a variation of Larry’s catchphrase “Pretty, pretty good.” The two Larrys situation makes for one hilarious (and uncomfortable) encounter after another, and Jon becomes so committed to the role he ends acting like Larry when he’s no longer around.