The 20 Best Curb Your Enthusiasm Guest Stars Who Frustrated Larry David

The 20 Best Curb Your Enthusiasm Guest Stars Who Frustrated Larry David

20

Elizabeth Banks

From the moment Elizabeth Banks entered Curb Your Enthusiasm in Season 9’s “A Disturbance In The Kitchen” by flirtatiously sending Larry a drink at a restaurant, she flipped the entire episode upside down. In half an episode, she flustered Susie Greene (Susie Essman) by comparing Susie’s teenage mentee going missing to her losing her cat, before helping get Larry arrested for dropping a rake on a cop car by overcomplicating a fake alibi with a horrendous Shakespearean acting. Few guest stars on this show have had as many jokes per screentime second land as Ms. Banks. —Keith Nelson

19

Abbi Jacobson

There’s not much to Jacobson’s Curb role as a country club dining room waitress with a stomach bug, and it’s far from the most mature humor the show has ever put on display. But let’s be honest for a second: a waitress announcing to an entire table of men that there may be issues with service due to her ongoing bout with diarrhea is just funny, whether you’re 16 or 61. It just is! And Jacobson sells the absurdity with the best of them, putting her Broad City comedy experience on grand display. —Evan Romano

18

Conan O’Brien

There’s room for the newest episodes on this list, too. Conan is a comedy genius, and the way he riffs with Larry—over things like conversational “clearance” granted via a conversation with Richard Lewis, borrowing a car, and throwing keys—lives up to the expectations. It’s two of the funniest people of television’s last 35 years “playing themselves,” but you can see in their eyes that they’re having just as much fun acting as all of us are having at home watching. —ER

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17

John McEnroe

Not so much an actor as just a cultural icon, former tennis star John McEnroe makes a fun appearance as himself in Season 6’s “The Freak Book,” getting driven around by a limousine that Larry has, through a bunch of the usual nonsense, found himself filling in and driving. McEnroe is quickly annoyed by Larry bugging him so much from the front seat, but they eventually bond and crack up hysterically while reading the titular coffee table book of freaks. It’s one of the most memorable guest star moments in Curb history. —ER

16

Martin Scorsese

Arguably the greatest director of all time came into Season 3 of Curb Your Enthusiasm, directing Larry as a mob boss in one of his movies, which showed off how naturally funny he’s always been. In just one minute of a scene, Scorsese explains why Larry pulling out a pair of cut off testicles wouldn’t read well in the scene they were filming. He receives a slap from Larry before gently scolding him for doing so. His dry but fast-paced way of instructing was a hilarious deflation to Larry’s penchant for long-winded opinions on how things should go. The two episodes he was in make you wonder how many unintentionally funny moments Scorsese made on the sets of movies like Gangs of New York and The Departed. —KN

15

Mekhi Phifer

a man in a suit and bow tie

HBO

Not many things capture 2005 more succinctly than the recurring presence of Mekhi Phifer—a good actor who should certainly be getting more work these days—in Season 5 as a private detective named Omar Jones. Omar is helping Larry throughout the season with an investigation into whether or not he’s adopted, and he’s damn good at his job. But it’s his stoicism when Larry questions things like his bow tie that make him a truly memorable presence. —ER

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14

Bill Buckner

As proven by Michael Richards in Season 7 and Lori Loughlin in Season 12, sometimes Curb Your Enthusiasm is the best vehicle for celebrities to poke a little bit of fun at their damaged public persona. Buckner, the late MLB player best known for allowing Mets player Mookie Wilson’s ground ball to pass through his legs in the 1986 World Series while he was a member of the Boston Red Sox, appeared in Season 8’s “Mister Softee,” making a similar costly error: allowing a Wilson-signed ball to pass through his hands and out an NYC window. But the story doesn’t end there: by the end of the episode, Buckner makes an acrobatic diving catch of a baby thrown from the window of a burning building. After decades of infamy, Buckner finally gets his moment of grand redemption. —ER

13

Bob Odenkirk

Appearing in the third episode of Curb Your Enthusiasm’s first season, Odenkirk as porn star Gil is the first great guest star appearance in the show’s history. Odenkirk’s uncanny ability to repulse and entertain simultaneously was on full display from the moment he called his home “The House that Cum Built.” His story about maintaining an erection on a porn set by having someone’s tobacco-smothered finger inserted in his butt is still one of the funniest bits in the show’s history. It’s a shame we never saw Porno Gil again after this episode, because the way he made Larry squirm in his skin was a sight to behold. —ER

12

Alanis Morissette

Season 3’s “The Terrorist Attack” is one of Curb Your Enthusiasm’s best episodes, and the presence of one of the most iconic rockers of the ‘90s is a major piece in making it all click. When the Jagged Little Pill artist is setting up shop at Larry’s house for an intimate NRDC benefit show, everyone shares their theory for what her “You Oughta Know” song is about. Throughout the episode, Larry cannot help but proclaim how good he is at keeping secrets, and Alanis herself falls victim to his false claims. She’s got some comedy experience under her belt from appearing in Kevin Smith’s Dogma, and while most of the funniest bits revolve around her presence rather than anything she’s doing, the late sight gag of her performing in a neck brace is one of the best Curb has ever come up with. —ER

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11

David Schwimmer

The Friends star embodied all of Ross’s high-pitched complaining and neurotic behavior when he was starring in the Broadway play The Producers in Season 4. Playing an exaggerated version of himself, Schwimmer argues with Larry about the cashew-to-raisin ratio in the snacks Schwimmer’s father sells and if Larry should be held responsible for finding and losing a watch Schwimmer already lost. Curb’s fourth and Friends’s final seasons ran simultaneously in 2004, so Schwimmer’s comedic jousting with Larry felt like two of the most popular styles of comedy in recent memory duking it out. Schwimmer more than held his own, and executed the best dance routine on stage with Larry in Curb history. —KN

10

Eddie Schweighardt

Eddie Schweighardt is definitely the youngest entry in the list of guest stars, but he deserves the honor for what he did as Greg in Season 8’s “Larry v Michael J Fox” episode. He plays the seven-year-old son of Larry’s girlfriend, Jennifer (Ana Gasteyer), whose flamboyance and love of fashion inspire Larry to describe him as “pre-gay” to his mother. Curb rarely includes kids in its episodes, and Greg utilizes his childlike exaggerations to fit right in by saying he would’ve beat up Hitler before explaining the design beauty of the swastika within a spastic dance. More than simply being a narrative device to catalyze Larry’s eventual scolding, Greg’s ear-splitting screech at being gifted a sewing machine and his controversial swastika pillow sham made him an unforgettable visitor to the Curb universe. —KN

9

Michael J Fox

Arguably the most shocking thing that happens in Curb Your Enthusiasm is that Michael J. Fox willingly uses the effects of his Parkinson’s disease to get laughs in Season 8. Parkinson’s being the reason Fox uses to explain why the soda he hands Larry explodes is comedic genius. It also inspired one of the funniest J.B. Smoove jokes about Fox hypothetically shooting semen in Larry’s face if he ever handed him his dick. Fox inspires former New York City mayor Michael Bloomberg to kick Larry out of NYC for doing the violin sign during his speech. If for nothing else, Fox’s guest star performance showed he can still perform at an elite level. —KN

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8

Jon Hamm

Jon Hamm will forever be best known as the smooth-talking, womanizing Don Draper at the center of Mad Men, but it’s a secret to absolutely no one that he loves—and excels in—the world of comedy (just ask anyone who’s seen Bridesmaids). After previously starring with Larry in his HBO film Clear History, Hamm showed up in Season 10’s “Elizabeth, Margaret and Larry” as himself, looking to shadow Larry before playing a similar character in an upcoming movie. Of course, Hamm eventually commits so much to his curmudgeonly role that—much like Larry—his unruly personality begins to gift him with some major problems of his creation. The visual sight gag of Hamm sticking his nose into a cup of Mocha Joe’s coffee, echoing Larry’s gesture from earlier in the season, is one for the ages. He even showed up again in Season 11’s “The Five-Foot Fence” for good measure. —ER

7

Rosie O’Donnell

Few people in Curb history posed as big of a threat to Larry’s fumbling attempts at dating as Rosie O’Donnell. Her final appearance on the show— Season 7’s “The Bi-Sexual”— is in the pantheon of Curb episodes, with O’Donnell and Larry engaging in a battle of the sexes when they serendipitously discover they’ve gained the affection of the same woman named Jane. She matches Larry’s wit, and then some, running with his baseball logic about the tie in their courtship battle going to the runner (i.e., heterosexual), and hitting him with juicing allegations after Larry’s Viagara-enhanced sexual performance with Jane prompts her to cancel her date with Rosie. Before that episode, she put her physical comedy on display while kicking Larry’s ass as they were wrestled over a check to decide who gets to pay for lunch. Don’t get me started on her dismantling Larry’s defense of himself not being an asshole, because he dates a disabled woman in Season 7’s “Denise Handicap.” —KN

6

Iris Bahr

As Orthodox Jewish woman Rachel Heineman in Season 5 of Curb Your Enthusiasm, Bahr stole every scene she was in thanks to the obsessive lengths she’d go to in order to follow her religion. Everything from burying plates—because she can’t have dairy and meat on the same plate—to literally leaping off a ski-lift with Larry to avoid being with a man after sundown, was on the table. The last time we saw her that season, she was calling her breast enhancements “festive” while demurely complaining about the back problems from them and dismissing Larry’s unwarranted criticism about her cosmetic surgery. She showed up again one last time in Season 9’s “Never Wait For Seconds” episode, accusing Larry of refusing to follow Jewish Orthodoxy by not jumping off the ski lift to remind us of one of the greatest Curb guest stars. —KN

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5

Chris Williams

There’s a reason J.B. Smoove wishes his character Leon, and Chris Williams’s legendary Krazee-Eyez Kila could’ve met. It’s because Krazee-Eyez Kila was knocking the most obscene jokes out of the park in a way only matched by Leon. As Wanda Sykes’s unfaithful rapper fiancé in Curb Your Enthusiasm’s third season, Krazee-Eyez Kila gets introduced to us getting advice from Larry about how many times he should say motherfucker in a rap verse where he compares breaking someone’s neck to the sound of a Rice Krispie Treat. Krazee-Eyez Kila exchanging racial terms of endearment with Larry and exploring Larry’s neck problems from oral sex showed us the vulgar depths Larry would go to with the right instigator by his side. —KN

4

Cheri Oteri

Saturday Night Live players are a fairly common sight on Curb Your Enthusiasm, as they tend to be in most major institutions within the comedy world. But the show’s veteran player, Oteri, is one of the best guest stars of Curb’s early seasons, playing the titular character in Season 3’s “The Nanny From Hell.” She’s perfect at capturing a comedic character who you can sense instantly that something is just a little off—and whose ultimate payoff and explosion makes everything in the episode fully tie together. Does anyone else have the Looney Tunes theme song stuck in their head? —ER

3

Bill Hader

Hader became an Emmy darling for creating and starring in HBO’s hit genre-bending series Barry, but he also earned an Emmy nomination for his impressive role as the titular characters (all three of ‘em!) in Season 11’s “Igor, Gregor, & Timor.” Hader has been a master of voices, characters, and bits since his days as a jack-of-all-trades on Saturday Night Live, and he’s rarely gotten a chance to be funnier than bouncing off Larry David and Jeff Garlin as this trio of scheming, eccentric characters. —ER

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2

Ben Stiller

Season 4 of Curb Your Enthusiasm produced some of the best guest actor performances, and Ben Stiller, as Larry’s nemesis, is right at the top. Tapped by Mel Brooks to be Larry’s co-star, he constantly blows up at Larry for not singing “Happy Birthday” with everyone else at his party and temporarily blinding him in one eye by accidentally stabbing him in the eye with a skewer stick in that same party. Stiller didn’t conceal his disdain for Larry under social niceties, especially when he tried to treat him like a chauffeur by sitting in the back seat when he was driving. Although they never ended up on the Broadway stage together, Larry and Stiller never had a dull scene on screen in Curb. —KN

1

Jason Alexander

Jon Hamm may have learned how to mirror certain aspects of Larry on Curb in Season 10, but Larry met his cynical match on Curb with Jason Alexander, who stepped into Larry’s psyche for nine seasons of Seinfeld as George Costanza. Ironically, the scene that made Alexander an all-time Curb guest happens in Season 2’s “The Car Salesman” when Larry and Alexander frustrate themselves into a grumpy stalemate arguing if George, and by proxy Larry, was a schmuck. Alexander’s face wrinkling in anger as Larry tried to defend the merits of George (and himself) being in a masturbation contest was meta gold. When you bring the Curb universe something as inane as acting without acting, you’ve solidified yourself a spot on this list. —KN

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