Larry David’s HBO sitcom Curb Your Enthusiasm is known for its big-name guest stars who play absurdly exaggerated version of themselves, just like David himself does. Not all of the guest stars play themselves; some play fictional characters. In fact, some guest stars – like Dustin Hoffman and Sacha Baron Cohen – make this the condition on which they appear on the show in the first place, because they don’t want to play themselves.
10 Philip Baker Hall (as Dr. Morrison)
It’s important to note that Philip Baker Hall is a highly respected actor. When you’ve seen him in countless Paul Thomas Anderson movies, you take him very seriously. That’s what makes Larry’s brazen disrespect for his character Dr. Morrison that much funnier. First, he berates Larry about using the phone in his office, which Larry denies is that big of a deal. Then, the two have a hilarious passive-aggressive back-and-forth about the “little prick” involved in the medical procedure.
Hall – who also played the library detective Bookman in Seinfeld – has returned to play Dr. Morrison a few times over the years, but never funnier than the time he drooled on Larry’s head in his office and, in turn, got drooled on by Larry at the theater.
9 Ricky Gervais
Ricky Gervais, a long-time fan of Seinfeld and Curb Your Enthusiasm, finally got the chance to lock horns with Larry in the eighth season. The British comedy icon played himself exactly how one might expect him to be: pretentious, irritating, and full of himself.
He gives Susie a signed copy of his own DVD as a gift, wears a $500 scarf to protect his vocal cords, has a hissy fit about Larry and Susie arguing through his performance, and insults Larry’s bread for being too hard. Of course, this is the same bread that Larry would later use to beat a mugger with to save him.
8 Bill Buckner
Curb’s guest stars often use the show to right their past wrongs in a satirical way. Bill Buckner, who famously cost the Red Sox a World Series with a fielding error, did this brilliantly in season 8.
After Larry’s error costs his softball team the championship, he can empathize with Buckner’s predicament. He is scorned out of a funeral for the error and misses a catch that lets Susie’s gift to Jeff fall out their apartment window. Finally, at the end of the episode, Buckner gets his redemption as he saves a baby from a burning building by diving through the air to catch it.
7 Steve Coogan (as Dr. Bright)
Steve Coogan’s turn as Larry’s bumbling therapist who tries to get him back together with Cheryl was hysterical. The poor guy gets put through the wringer as he tries to correct his own mistakes.
Larry gets him to mug Cheryl’s therapist so he can swoop in and look like a hero, then he gets pinched by the cops, then he comes out of prison with no idea what he wants to do with his life. Coogan is a terrific comic actor whose talents translate perfectly into the improvised world of Curb Your Enthusiasm.
6 Martin Scorsese
In season 3, Martin Scorsese casts Larry David to play a mob boss in his latest movie, having once seen him yelling at the audience in a comedy club in New York and been convinced that he could play the character’s rage. Scorsese plays himself pretty much as one would expect, as a no-nonsense director who wants to get the perfect take.
But what makes him a great guest star is how Larry interacts with him. Several takes in, Larry asks Marty, “Do you even know what you’re doing?” This is Martin Scorsese, the legendary filmmaker behind Goodfellas and Raging Bull!
5 Shaquille O’Neal
Season 2’s “Shaq” is one of the most memorable episodes of Curb, because it begins with one of the greatest celebrity cameo appearances and leads into a great arc for Larry’s character. When he accidentally trips Shaquille O’Neal while sitting courtside at a Lakers game, Larry is booed out of the stadium as he’s thought to have planned it.
But then he realizes, with everyone hating him, he doesn’t have to do anything for anyone – and he can get away with saying whatever he wants. And then when he makes things up with Shaq, he’s back to normal again.
4 Lin-Manuel Miranda
God knows how Larry managed to get Lin-Manuel Miranda – arguably the hottest talent in the world right now – to make the time in his busy schedule to appear in a multi-episode story arc that makes him look like a terrible person. But either way, it’s a good thing he did, because it saved the latter half of season 9.
Miranda plays himself exactly how one might picture the worst version of him to behave: an arrogant, smug, ungrateful, self-obsessed perfectionist. He’s probably nothing like that in real life, but he plays it perfectly. Plus, his arc ends with the most hysterical reference to the Hamilton v. Burr duel.
3 Ben Stiller
Ben Stiller played himself in season 4 as Larry’s co-star in The Producers. Stiller played every scene against David perfectly, whether they were arguing over David sitting in the front of Stiller’s car, David not singing the “Happy Birthday” song at Stiller’s birthday party, or David accidentally stabbing Stiller in the eye with a used skewer.
It’s difficult to keep up in an improv situation, especially when you’re working with seasoned pros, you’re new to the show, you have to serve the motivations of a scene, and above all, you have to keep it funny. Ben Stiller nailed every scene he was in.
2 Chris Williams (as Krazee-Eyez Killa)
Krazee-Eyez Killa was sort of an early template for Leon, Larry’s black, streetwise sidekick. He came into the show for one episode as a rapper engaged to Wanda Sykes, and Chris Williams brought everything to the character. He even wrote the rap lyrics that he pitches to Larry, which Larry wasn’t expecting at all.
He took a character that wasn’t very developed or fleshed-out and really made it unforgettably his own. Williams also immortalized a litany of memorable quotes in just a few short appearances, from “I’m your motherf****n’ Caucasian!” to “Yo, Delicious, get a tissue – my man’s gonna sneeze!”
1 Michael J. Fox
In the comedy world, there’s a big distinction between “punching up” and “punching down.” Sensitive subjects can be used for comedy, but only if they’re handled in the right way and if the targets are right. The season 8 finale “Larry vs. Michael J. Fox” sees Larry going head-to-head with Michael J. Fox and the episode wrings a lot of humor out of Fox’s affliction with Parkinson’s disease.
From a soda can getting shaken up to Larry being mistaken for playing a fake violin, none of the humor is mean-spirited or insensitive, because the targets are right, and Fox is never the butt of the joke – only Larry is.