Larry David and Lin-Manuel Miranda in Season 9 of 'Curb Your Enthusiasm.'
John P. Johnson—HBO
January 17, 2020 2:08 PM EST

Last October marked 20 years since Curb Your Enthusiasm debuted as an hour-long special that would soon morph into a long-running series. Though there have been multiple hiatuses between seasons—presumably for creator Larry David to mine his anxieties for compelling story arcs—Curb has continually returned to add its own fresh dose of awkwardness to an evolving culture.

Throughout its run, Curb has consistently featured notable, often delightful casting of famous faces in shocking and uncomfortable situations. These guest stars have ranged from niche comedians yet to establish themselves to comedy legends giving unexpected performances. In anticipation of Curb Your Enthusiasm‘s 10th season, premiering on HBO on Jan. 19 and set to include cameos from Jon Hamm, Laverne Cox and Jane Krakowski, TIME revisits the most memorable of those many cameos.

Though noteworthy names like Ted Danson or members of the cast of Seinfeld, which David co-created, show up on Curb often, we’ve excluded from this list anyone whose regular inclusion makes them more of a featured player than strictly a cameo. Below, the 12 performers who most surprised us when they appeared—and left us wanting more when they left.

Bob Odenkirk

In the third episode of the first season, Larry and Cheryl David (Cheryl Hines) attend a dinner party hosted by a former porn star named Gil, played by Bob Odenkirk. Though the episode, which aired in 2000, took place after Odenkirk became a somewhat familiar face with his influential HBO sketch comedy show Mr. Show, he had not yet broken into the mainstream.

In the episode, titled “Porno Gil,” Odenkirk’s Gil tells awkward stories about his past work. The episode sticks the landing as Larry later stumbles on one of Gil’s pornographic movies (classily titled Motel Dick). The guest spot is a hilarious example of Odenkirk’s absurd comedic stylings, which are far better seen than described. It would be almost another decade before Odenkirk took on the classic character Saul Goodman (née Jimmy McGill), first in Breaking Bad and then as the eponymous character in Better Call Saul. But his turn in early Curb is a great reminder that Odenkirk always deserves more screen time.

Shaquille O’Neal

In Season 2, Larry makes a catastrophic outing to a Los Angeles Lakers game, where he has court-side seats. There, his outstretched legs get in the way of Shaquille O’Neal’s hustle, sending the legendary basketball player to the ground and then to the hospital. Shunned by friends and family for injuring the player, Larry takes it upon himself to visit Shaq in the hospital and try to make amends.

Shaq’s cameo in Curb is not only great because the circumstances around it are so ridiculous, but also because the athlete’s turn is so charming and genuinely funny. Come for Shaq insisting that peanut butter has dairy in it, stay for his stanning of Seinfeld.

Cheri Oteri

In Season 3, Larry’s inability to respect other people’s house rules leads to the firing of a peculiar nanny, played by Saturday Night Live alum Cheri Oteri. It’s an unforgettable portrayal by Oteri, full of exceptional improv in a classically outlandish Curb character.

In the episode, Oteri’s nanny visits Larry’s house after getting fired for letting him use a host’s private bathroom. The nanny immediately seems a little off, having admitted to spending years working in the Six Flags Magic Mountain Looney Tunes Lodge. Her screws keep loosening as Larry tries to pawn her off on friends Jeff and Susie (Jeff Garlin and Susie Essman), both to assuage his guilt and to fill their newfound need for a nanny. Things, as they do in Curb, come crashing down, but luckily in this episode, there’s plenty of discarded sponge cake to break the fall.

Wanda Sykes

Wanda Sykes’ Curb appearances, in which she plays a savage version of herself, always ready to spar with Larry, are among the many pleasures of the show’s casting. From the first season to the most recent, Sykes sporadically shows up as both a friend to Cheryl and a foil to her husband.

An enormously gifted comedian in her own right, Sykes’ volatile chemistry with Larry makes her an unforgettable Curb cameo. Larry’s relationship with women on the show is often contentious, but most characters prefer to ignore and escape his relentless egotism. Sykes, like Susie Green, offers the ultimate challenge to Larry’s boundless, ill-advised confidence. She is the immovable object to his unstoppable force, and it’s a lot of fun to watch.

David Schwimmer

Curb’s fourth season is all about Larry starring in a Broadway production of The Producers. And though his Max Bialystock is originally played opposite Ben Stiller’s Leo Bloom, when David Schwimmer takes over the role of Bloom mid-season, one of the standout Curb cameos is born.

The best cameos take a face everyone already knows and imbue it with a personality or characteristic that viewers don’t see coming. Schwimmer’s appearance on Curb coincided with the end of Friends. He had spent 10 years as goofy, dorky Ross Geller, and it was unexpected, to say the least, when he showed up as a stuffy, grumpy foil to the bouncy, boyish Larry David. We had already seen Stiller playing a jerky version of himself in many previous cameos; Schwimmer’s dour portrayal was a welcome gift.

Mel Brooks and Anne Bancroft

You can’t talk about Curb’s fourth season without discussing Mel Brooks’ role as himself. It would be enough for the comedy legend to have shown up in Curb at all, just for the pleasure of seeing his face, but Brooks’ appearance offers much more. As well as being a delightful version of himself and giving musical lovers a peek behind The Producers, Brooks also delivers the season-long arc’s big punchline. And it’s one of Curb’s smartest.

Despite Larry angering his co-stars and lazing his way through the rehearsal period, Brooks pushes for him to play Max Bialystock all season long, much to the chagrin of those around him. Larry seems to prove those naysayers right on opening night, which takes place in the season finale. He completely forgets his lines in one of the show’s early scenes and the audience heads for the door en masse. That’s when Brooks reveals that he cast Larry because he knew it was a bad idea and would set him free of the show. Brooks wanted the show to fail for his own personal gain, much like the plot of The Producers itself.

In their wonderful appearance, Brooks and his off-screen wife Anne Bancroft (who made the cameo a year before she died) rejoice as the show seems to crash and burn. And as Larry uses the forgotten lines to his advantage, delighting the returning audience, Brooks and Bancroft wail over their cursed luck.

Stephen Colbert

Curb’s fourth season was a good one for cameos, and we’d be remiss to omit the brief but memorable appearance of Stephen Colbert in the season finale. Colbert plays a New York tourist who asks Larry to take a picture of him and his wife. A spat erupts as Larry feels unable to take a picture and Colbert realizes they will see Larry in The Producers during their trip. With dramatic flair, Colbert casts a curse on Larry, and predicts he will fail in the show.

Colbert’s Curb cameo occurred while he was still one of Jon Stewart’s rotating “reporters” on The Daily Show, before he made the leap to The Colbert Report. Though he’s only on Curb for a few minutes, the comedian’s electric comedic energy proves unforgettable.

Dustin Hoffman/Sacha Baron Cohen

Dustin Hoffman and Sacha Baron Cohen fairly take up one spot in this cameo list; they appear side by side during the same scene, both credited as “Larry’s Guides” in introducing Larry to the afterlife.

The whole of Season 5 revolves around Larry vowing to change his life after a near-death experience and deciding to donate a kidney to his best friend, comedian Richard Lewis. The arc ends with a problem on the operating table and Larry actually dying. Enter Hoffman and Cohen, who somewhat patiently welcome Larry into a heavenly place. Their patience gets tested, however, as Larry remains Larry, even in paradise. They ultimately decide Larry must wait on his place in the clouds, putting off his dream of meeting Seinfeld-fan Marilyn Monroe and keeping the hair that blessedly appeared on his head.

Hoffman and Cohen aren’t on the screen for long, but they serve as more than stunt casting. Their humor build alongside the tension, and it’s good fun watching an angel argue with the newly deceased over how to correctly store DVDs. (The scene admittedly plays a bit differently all these years later; in 2017, several women accused Hoffman of sexual misconduct spanning several decades, to which the actor responded with a mix of denial and apology.)

Steve Coogan

In Season 6, after years of suffering, Cheryl leaves Larry. Much of the plot of the next two seasons deals with Larry trying to win her back in various ways. Perhaps the most outlandish scheme, and the most damaging to any one character, involves Steve Coogan’s cameo in the episode titled “The Therapists.” Coogan plays Larry’s therapist, who believes himself to be in something of a battle of wits against Cheryl’s therapist. He sends Larry on a mission to undermine the other therapist’s advice, resulting in a comedy of errors. It’s a classic, twisted Curb story of schemes gone wrong, leading to bad luck and worse consequences. The twist is that it’s largely Coogan who pays the price instead of Larry.

At the beginning of the episode, Coogan plays a pretentious, snotty character, a familiar angle for the performer. However, in what almost feels like penance for his long career of pompous portrayals, he is put through the wringer on Curb. He’s belittled for giving bad advice, he’s humiliated when he’s arrested for setting Larry up to be a hero and he’s broken when left in jail for the duration. It’s a surprising turn for Coogan simply because he plays a beaten cur as well as he plays a boorish snob.

Michael J. Fox

Larry goes back to New York City in Curb Your Enthusiasm’s Season 8, which yields great cameos from the likes of Rosie O’Donnell, Ana Gasteyer and Ricky Gervais. But the most striking cameo of the season is Michael J. Fox, playing himself, as a neighbor who lives above Larry’s rented NYC pad.

Fox brought to Curb that element of surprise that makes for the best cameos: we don’t necessarily expect him on an improvised comedy show at all, let alone making light of his Parkinson’s disease. In the show, Fox again and again claims that his condition is to blame for slights to Larry: a soda shaken up too much, a habit of treading heavily on his floor/Larry’s ceiling. But Fox’s delivery is so solid, it made us hungry for more pure comedic roles from the longtime star.

Carrie Brownstein

When Carrie Brownstein makes her appearance at the beginning of Season 9, it’s only natural to wonder what took the show so long to cast her. In her cameo, she plays an incompetent assistant to Larry, riddled with self-diagnosed problems and yet impossible to fire. Larry says her character was “foisted” (which is also the name of the episode) on him by a glowing recommendation from Jimmy Kimmel. In turn, Larry spends much of the episode trying to foist Brownstein’s character onto someone else.

Brownstein, best known as a founder of the rock band Sleater-Kinney and for co-starring in eight seasons of the sketch show Portlandia, is a natural fit for a role on Curb. Portlandia was reportedly mostly improvised, and in her brief time on screen in Curb, she brings an immense comfort with both the unscripted language and the awkward humor the show had developed over 17 years. Even though Brownstein mostly has to contend with the subject of constipation in her episode, she gets everything she can possibly squeeze out of the topic. And when Larry does indeed foist her off onto Susie (which is exactly what happens with Cheri Oteri’s nanny), it hard not to wish Brownstein had gotten a lot more time on Curb Your Enthusiasm.

Lin-Manuel Miranda

Curb Season 9 aired in 2017, a full six years after the previous season. And, as if to prove the show never lost its firm grasp on pop culture, it cast one of the most ascendant stars in the world to play himself for the final two episodes.

In keeping with many on this list, Lin-Manuel Miranda’s cameo plays the star against type, with the usually-charming Miranda playing himself as a petty micromanager who demands to get his way. His portrayal shows off extremely good comedic timing in his volley with Larry, and the setup is inherently hilarious: as Miranda assists in the production of Larry’s musical Fatwa!, it’s a pleasure to see him countering Larry’s creative control while poking fun at himself. His cameo is a perfect encapsulation of the masterful way in which Curb uses unexpected casting to its advantage. Here’s hoping for more of the same in Season 10.

Contact us at editors@time.com.

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