Throughout its 10 seasons, Curb Your Enthusiasm has continuously delved into uncharted territory, pushing the envelope and crossing every politically correct boundary possible in the name of humor.
Though the acclaimed HBO comedy series has an incredibly strong core cast, with comedic talents such as Larry David, J.B. Smoove, Susie Essman, and Jeff Garlin carrying much of the show, Curb is almost always at its best when an equally bold guest star is involved. And since this is Larry David's world after all, more often than not, the guest star soon manages to become one of Larry's many, many nemeses.
Season 1: Bob Odenkirk
Before he was known for his work in the Breaking Bad franchise, comedian Bob Odenkirk appears in the first season episode "Porno Gil" as, well, Porno Gil.
A former adult film star, Odenkirk's Gil is a completely off-color character, but Odenkirk's dry, totally committed delivery of every dirty tale and less-than-comfortable joke makes him a guest star to remember — if not a particularly enjoyable character.
Season 2: Shaquille O'Neal
Larry's misadventures in every aspect of his life lead to yet another memorable guest star interaction. In the second season episode "Shaq," Larry trips Shaquille O'Neal during a Lakers game, seriously injuring him in the process.
The episode allows Shaq the chance to shine and show off his comedy skills when Larry visits him in the hospital. In particular, Shaq excels in leaning into the goofy clueless jock stereotype while playing Scattergories, where he insists that peanut butter is a dairy product, and eventually fires his personal team doctor after Larry's advice.
Season 3: Chris Williams
As the new boyfriend of recurring player Wanda Sykes, Krazee-Eyez is a foul-mouthed, quick-witted rapper who somehow becomes buddies with Larry. They bond over Larry's oddly insightful rap lyric edits and sexual exploits, and though this friendship is short-lived, Williams' commitment to the role is one for the ages.
Season 4: Stephen Colbert
Sometimes, all a guest star needs to steal the show — and the season at that — is one very short scene. When comedian and eventual talk show host Stephen Colbert appears in a fourth season episode of Curb, he does so as the vaguely named "Tourist Man."
In one of Larry's legendary nonsensical feuds, Larry gives Colbert's tourist and his wife a hard time when they ask him to take a photo. Larry's single interjection leads to the unraveling of Colbert's character's marriage, as well as Colbert proudly threatening that Larry's production of The Producers will be a failure.
Season 5: Wanda Sykes
Wanda Sykes is a comedic talent who appears many times throughout the series, but arguably her best, most hilarious, and also most offensive appearance comes in the fifth season episode "The Bowtie." Wanda's storyline in this episode centers around Larry's adoption of a new dog named Sheriff.
Convinced beyond all disbelief of the fact that this dog is racist against Black people, Wanda launches into a truly memorable tirade against Larry, Cheryl, and the dog alike — which she dubs "that Klan dog." (And as it turns out, the dog isn't just racist; he's homophobic, too.)
Season 6: Steve Coogan
Arguably one of Larry's most poorly thought-out schemes winds up involving guest star Steve Coogan's poor character of Larry's therapist, Dr. Bright. After Cheryl's therapist discourages her from reconnecting with Larry, Larry enlists his own therapist into a plot to try and curry favor with Cheryl's therapist.
After Leon backs out of the poorly concocted plan, Coogan's Dr. Bright is brought in to play the role of a feigned mugger attacking Cheryl's therapist, whom Larry gallantly fights off. Of course, everything goes absolutely wrong, resulting in Dr. Bright being taken into custody and losing his medical license. Coogan's commitment to the rapid downward spiral is pitch-perfect.
Season 7: Philip Baker Hall
Yet another medical professional finds themselves the unwitting subject of Larry's torment, and it allows another guest star to shine in the legendary Philip Baker Hall. As Larry's physician Dr. Morrison, Hall makes a couple of appearances in the series, but it's his second appearance in the series' seventh season that really stands out.
The episode "The Hot Towel" finds Hall's Dr. Morrison being forced to give Larry his personal phone number for medical consult, and naturally, Larry abuses the privilege every chance he gets, leading to plenty of opportunities for Hall's curmudgeonly humor to shine.
Season 8: Michael J. Fox
In the eighth season finale, aptly titled "Larry vs. Michael J. Fox," Larry finds perhaps his most memorable nemesis of them all in his New York neighbor, the actor Michael J. Fox. Though it's arguably one of the series' more offensive episodes, as the humor and drama alike both hinge upon Larry's misunderstanding of Fox's Parkinson's, Fox nevertheless proves himself to be totally up for the task of taking Larry on.
The episode finds Larry and Fox at odds with one another time and again, through miscommunications at a night club, a shaken soda, noisy shoes, a poorly timed hand gesture, and more. All throughout, Fox is nothing short of a comedic genius.
Season 9: Lin-Manuel Miranda
Yet another beloved celebrity finds himself running afoul of Larry David in the final two episodes of the series' ninth season: Lin-Manuel Miranda. Appearing as himself in order to help Larry produce his latest musical project, Miranda is immediately at odds with Larry over everything from who sits behind a desk to Hamilton tickets.
Of course, Larry falls asleep while attending Hamilton, and through an entirely unrelated series of events involving Miranda's family, the two men engage in a duel of their own sorts while playing paintball.
Season 10: Jon Hamm
If there were ever an unlikely actor to take inspiration from Larry David for a character, and to do so with absolute startling accuracy, it would be Jon Hamm. Nothing about Hamm remotely suggests that he would be the type to embody Larry, of all people, but Hamm's recent streak of post-Mad Men comedic performances reaches an all-time high in this role.
In perfectly embodying Larry in all his many, many, many ugly faults and absurd behaviors, even taking exceedingly detailed notes along the way, Hamm gives one of the best performances not just in the series, but in his entire career.