A Taxonomy of Curb Your Enthusiasm Guest Stars

The 20-year run of Curb Your Enthusiasm — accounting for plenty of long breaks between seasons — continues when the HBO series returns for a 10th season on Sunday. As in past seasons, there will be plenty of celebrity guest stars to spar with Larry David in the ten new episodes, including Jon Hamm, Laverne Cox, Fred Armisen, Kaitlin Olson, Jane Krakowski, and Wilco frontman Jeff Tweedy.

The nine previous seasons have brought us many appearances from comics, actors and actresses, sports heroes, and even future presidential candidates (Michael Bloomberg appeared in the Season 8 finale and has the clip on his official YouTube account). Have they all been great? Sadly, no. There's a wide variance between a beloved talent doing a knowing heel turn on the show (F. Murray Abraham last season) and someone who brings more name recognition than talent to the proceedings (a smoking-jacket-wearing Hugh Hefner). Below is a comprehensive look back at some of the show's best, worst, and most notable guest stars*.

* What constitutes a guest star? For the purposes of this roundup, it's anyone who has been featured in fewer than 10 episodes, or a whole season's worth of Curb, which rules out series regulars Jeff (Jeff Garlin), Cheryl (Cheryl Hines), Susie (Susie Essman), Richard (Richard Lewis), Marty Funkhauser (RIP, Bob Einstein), Leon (J.B. Smoove), Nat David (Shelley Berman), Loretta Black (Vivica A. Fox), and a few other recurring characters.

Guest Stars Playing Themselves

One of the hallmarks of Curb is well-known personalities playing exaggerated or fictionalized versions of themselves, an HBO tradition that goes back to The Larry Sanders Show. Just as Larry David is playing an amped-up version of the very-well-off co-creator of Seinfeld, many of the people he deals with on the show follow suit.

Best Guest: Michael J. Fox did a spectacular job tweaking his nice-guy image in "Larry vs. Michael J. Fox" (Season 8, episode 10), in which Larry suspects the actor, who happens to be his neighbor on the show, might be faking the extent of his Parkinson's symptoms. Fox popped up again in the following season for "Never Wait for Seconds" (S9E8) in a callback to his fight with Larry.

Worst Guests: Season-long arcs don't always pay off so well, and Season Four's gambit that Larry is cast in a production of The Producers with David Schwimmer lands with a thud in "Opening Night" (S4E10), in which a cackling Mel Brooks and Anne Bancroft (may she rest in peace) reveal that they're purposely tanking the show, mirroring the plot of The Producers. It's not that they're so bad, but the on-the-nose scenario just wasn't worthy of their talents.

Dishonorable Mention: By the same token, last season's appearances by Hamilton creator Lin-Manuel Miranda felt like a repeat of past plots, with the star brought in to help Larry with his Broadway show about Salman Rushdie. In the episodes "The Shucker" (S9E9) and "Fatwa!" Miranda makes the obvious turn of trying to hip-hop up the show to Larry's chagrin, and the chemistry never quite meshes. Larry should really stop trying to make Broadway a thing on Curb.

Larry's Friends

Larry David keeps a pretty tight circle of close friends on the show, particularly Jeff Garlin, Marty Funkhouser, and Leon Black, but among guest stars a few have stood out and reappeared multiple times.

Best Guest: Jerry Seinfeld stayed away from Curb for so long (except for a hilarious cameo in the aforementioned Producers episode where he leaves his theater seat as the show starts to bomb) that when a Season 7 arc about a Seinfeld revival began, it felt overdue. Larry and Jerry's chemistry was solid for the whole season, and the show's what-if revival was probably better than any real one could have possibly been.

Worst Guest: Chris Williams as Krazee Eyez Killa (S3E8) is a great performance of a character that hasn't aged so well and which was clearly the template for J.B. Smoove's Leon: a black man explaining black culture to Larry all the time.

Honorable Mention: Rosie O' Donnell and Larry appear to get along great on the show until they don't, whether it's literally wrestling in a restaurant over who's paying the check in "Denise Handicapped" (S7E5) or competing for the same woman in "The Bisexual." (S8E7).

Larry's Enemies

It can sometimes be hard to tell Larry's friends from his enemies, as he tends to piss off even his closest pals regularly. But there are plenty of people on the show who clearly don't like anything about Larry.

Best Guest: Wanda Sykes comes in just under the guest-star wire with nine appearances, though it felt like she was a constant presence in early seasons as one of Cheryl's best friends who always had a problem with Larry's behavior, particularly toward women and African-Americans, such as the time Larry fired an employee in "The Benadryl Brownie" (S3E2).

Worst Guest: Ricky Gervais. Nope, sorry, no. Not funny, not a great appearance, just a bunch of awkward needling as Larry and Ricky take an instant dislike to one another in "The Hero" (S8E6).

Honorable Mention: Sofia Milos played Richard Lewis's girlfriend in the show's first season, starting with "The Pants Tent" (S1E1), and, along with Susie Essman, set the tone for a long string of wives and girlfriends in Larry's circle of friends who hate his guts.

Larry's Romantic Partners

For many years of the show, Cheryl was Larry's romantic foil, but mirroring his real-life divorce, the couple broke up in Season 6. Since then, Larry has had a string of sexual encounters and short-lived relationships, most notably with Vivica A. Fox as Loretta Black (she just missed the list with 11 Curb appearances.

Best Guest: Anne Bedian as Shara, who made for one of the show's most hilarious and expletive-filled romantic encounters in "Palestinian Chicken" (S8E3). She returned for more hate sex in "The Pickle Gambit" (S9E2).

Worst Guest: Elizabeth Banks was a great casting idea and brought a loopy energy to the show in her episode "A Disturbance in the Kitchen" (S9E3), but the pairing ended too abruptly, and since she was playing herself, it didn't seem all that believable that she'd be into Larry.

Honorable Mention: It's easy to forget that Larry's first post-Cheryl date was with Lucy Lawless, who plays a charming version of herself in "The TiVo Guy" (S6E7). She acquits herself best by being reluctant to jump into bed with Larry (smart lady!).

Cringiest Guests

Even on a show that thrives on awkward situations, a few guest stars have gone above and beyond in helping Larry David approach taboo subjects.

Best Guest: Survivor contestant Colby Donaldson has one of the show's funniest and most memorable dinner-party arguments with a Holocaust survivor over the definition of the word in "The Survivor" (S4E9).

Worst Guest: Monena, the prostitute who helps Larry drive in the carpool lane, never rises above a really unfortunate stereotype despite committed work from Kym Whitley in "The Carpool Lane" (S4E6).

Honorable Mention: Sierra McCormick played a 9-year-old in "The Table Read" (S7E9) who begins texting Larry after her mother tells him that the girl has a "rash on her pussy." One of the show's weirdest, cringiest turns is also one of its funniest.

Dearly Departed Guests

The show has gone on so long that it's inevitable that some of its guest stars will have passed on by now. A moment of silence, please.

Best Guest: Baseball player Bill Buckner famously lampooned his real-life 1986 between-the-legs error that cost the Boston Red Sox the World Series and gets redeemed by saving a baby in "Mister Softee" (S8E9). Buckner passed away last year.

Worst Guest: Hugh Hefner looks like he can barely stand in 2005's "The Smoking Jacket" (S5E6), an episode that mostly feels like an excuse to shoot at The Playboy Mansion. Hefner died many years later, in 2017.

Honorable Mention: The great Joan Rivers made an appearance early on Curb in "The Benadryl Brownie" (S3E2), lampooning Richard Lewis on an award-night red carpet. Rivers died in 2014.

Most Surprising Guests

Sometimes the best guest stars on Curb are the ones we never expected, or the ones who seem so out of place many years later.

Best Guest: Bea Arthur appeared briefly as Larry's mother, who berates him in heaven when he has a near-death experience for "The End" (S5E10). "What kind of schmuck are you?!" she begins, angered that he agreed to donate a kidney. It's a delight.

Worst Guest: Sure, he's an easy punching bag, but it's hard to account for hip hop wannabe and accent appropriator Chet Hanks getting a two-episode role on the show as a soldier dating Jeff's daughter, including the episode "Thank You For Your Service" (S9E5).

Honorable Mention: We've seen Eric André play it straight before on TV, but it's still strange to catch the manic host of The Eric André Show as a P.A. on the set of the Seinfeld revival in two episodes including "Seinfeld" (S7E10).

People are talking about Curb Your Enthusiasm in our forums. Join the conversation.

Omar L. Gallaga is a longtime technology and culture writer with bylines in The Wall Street Journal, NPR's All Tech Considered blog, Rolling Stone, The Washington Post, CNN and the beloved TV websites Television Without Pity and Previously.tv. He's a former newspaper journalist who now lives in New Braunfels, Texas. You can find him on Twitter @OmarG.