Life, Larry, and the Pursuit of Unhappiness: A Guide to Every Major Guest Star

The limited series, co-written and directed by David’s longtime collaborator Jeff Schaffer , consists of sketches that cover key moments from the past of this great country, including highlights of the American Revolution, important events in civil rights history, and innovations in technology. Some of the messaging is very familiar to Curb Your Enthusiasm fans who spent 12 seasons watching “Larry” complain about minor social injustices; other sequences don’t hold back at all with their politics.

The guide below is drawn directly from the closing credits of each episode, and will be updated each week as new episodes premiere. It should be unnecessary to specify which characters are being played by David. (He’s the bald guy who’s probably yelling.)

One last note, before we begin: Don’t drink every time someone who was on Curb Your Enthusiasm shows up. Your liver will thank you.

[ Editor’s note: The following contains spoilers for Life, Larry, and the Pursuit of Unhappiness Episode 7, “Lawrence.” ]

The series begins with our former President singing the praises of our great country, while also managing to throw some arguably deserved shade at Larry David. Then, we get our first taste of Samuel L. Jackson’s dry but hilarious work as the series’ narrator, his contributions essential to setting up each individual moment of history featured in this series.

The first sketch features David as Robert Livingston, who’s trying to include some additional complaints to the grievances section of the Declaration of Independence. Alas, his ideas get soundly rejected by his fellow revolutionaries, played by the always wonderful Henry Winkler, Chris Parnell, and Alan Tudyk.

The series then moves onto the invention of the telephone, with David as Alexander Graham Bell and veteran comedy actress Mo Gaffney as his supportive wife Mabel. Richard Kind is the other big guest star, playing the famous receiver of the very first phone call, because by law, all comedy shows are required to feature Kind in some capacity.

Additionally, there are three spectators in the crowd who may look familiar: Alison Becker been a recurring guest star on many shows (including Curb ) but is most famous to me as lovelorn Shawna Malwae-Tweep from Parks and Recreation . Mary Sohn was a key member of A.P. Bio ’s very funny ensemble and appeared in Freakier Friday and the Showtime series Work in Progress . And Rodney J. Hobbs’ credits include The Office , Modern Family , First Man , and the Nickelodeon comedy Young Dylan .

The World War I sketch features Michael Chiklis as the gruff Sergeant who orders Larry into battle, a perfect use for the star of The Shield and multiple Fantastic Four movies. (He was once, also, The Commish !) Playing Larry’s fellow soldiers are Mike Castle, a Comedy Bang Bang and Curb alum, and Jake Reiner, whose past credits include playing reporters on American Crime Story , For All Mankind , and Ice Cube’s War of the Worlds . Reiner additionally appeared on Curb , and happens to be the son of Rob Reiner and Michelle Singer Reiner.

In the final sketch, Jurnee Smollett plays Rosa Parks, and not only is the sincerely fantastic Friday Night Lights and Birds of Prey star more than a match for the antics of “Murray,” but she does bear a strong resemblance to the civil rights hero. No spoilers for what’s to come, but she won’t be this show’s last bit of brilliant casting.

Episode 2 of Life, Larry and the Pursuit of Happiness features the show’s most viciously political sketch to date. That, however, comes after reuniting David and Jerry Seinfeld as Lewis & Clark, the famed explorers who, in this version of events, were mostly just excited to get away from their wives for an extended fishing trip. Playing Lewis’s wife is the fantastic Rita Wilson, who manages to avoid being too shrewish in her disapproval of her husband and husband’s best friend’s plans.

Then comes the Tilden sketch, which plays more like an extended opportunity for David to rant at length about the electoral college, an American institution that perhaps deserves this level of ire. Playing his aides are Matthew Jones and Rich Fulcher, the former has made frequent guest starring appearances across shows including Curb Your Enthusiasm , while the latter is a familiar face to fans of The Mighty Boosh and Drunk History .

The Great Depression segment features David getting in some beautiful riffing with Larry Wilmore, quietly one of comedy’s most important voices, and an appearance by Colton Dunn as the server of soup. Dunn was a series regular on Superstore , a writer, co-producer, and occasional performer on Key & Peele , and is now a frequent guest star across a wide range of series, while also serving as a writer and supervising producer on Apple TV’s 2026 hit series Widow’s Bay ! The real standout of the sketch, though, is Kaley Cuoco’s grieving widow, as the Big Bang Theory and Harley Quinn star proves her comedy instincts are more than a match for David’s.

Finally, we have a sketch built around a committed posthumous performance from Rob Reiner as George Washington, who explains to a lively crowd why he won’t be seeking a third term in office. There’s not a lot of subtlety here in the messaging, I mean, could you imagine an American president choosing not to respect the results of a free and fair election and instead encouraging an insurrection?, especially when Jimmy Kimmel pops up as “Crowd Member #1.”

Another crowd member is played by Allan Havey, perhaps most memorable as Mad Men ’s Lou Avery (never forget the “Scout’s Honor” comics), but it’s really Reiner’s moment in the sun, and a bittersweet reminder of how much he’ll be missed.

Episode 3 opens with a sketch reflecting on the Boston Tea Party, with Lin-Manuel Miranda (a guy you could say knows a little bit about the American Revolution ) as one of the ringleaders. (For some reason, he decided not to invite David’s barrel-maker to the festivities.)

In addition to Miranda, veteran comedian and writer Lou DiMaggio played the barrel-maker’s friend (who, yeah, might have heard about the Tea Party beforehand but didn’t tell Larry about it). Also on the boat having fun with tea were Jordan Black, perhaps most memorable as Dean Spreck from Community , and Brad Morris, whose recent credits include The Bear , The Comeback , and many episodes of Great News . Plus, you might not be shocked to learn that all of the aforementioned gentlemen… guest-starred on Curb .

Speaking of Curb , the Underground Railroad sketch largely played like an opportunity for David to once again riff hardcore with J.B. Smooth, who was a series regular by the end of the HBO comedy’s run. Jonesy’s fellow seekers of freedom, meanwhile, were played by Dean Sharpe, who’s guest-starred on shows including not just Curb , but Brooklyn Nine-Nine , Black-ish , and Mrs. Davis , and Tru Valentino, a past series regular on The Rookie and also a voice actor on shows like the revived Beavis and Butthead and Spidey and His Amazing Friends .

After that, Pursuit of Unhappiness made fun of airplane travel with Mad Men Emmy winner Jon Hamm and Will & Grace Emmy winner Sean Hayes as the Wright brothers. Then, the episode wrapped up with a rare example of David playing the central historical figure in a sketch: the notorious Senator Joseph McCarthy. Spinal Tap and Better Call Saul star Michael McKean appears as Joseph Welch, the lawyer who famously asked McCarthy, “Have you no decency, sir?” while silver fox Rob Huebel, one of TV’s most prolific comedy actors, played another senator helping to moderate the proceedings.

Last week’s episode, to put it in the most ladylike terms, was a straight-up sausage fest, so it’s nice that there’s a little more feminine energy in this week’s guest cast (even if one of the biggest female roles is played by David himself). The first sketch, though, is a two-hander recreating the famous parking garage scenes from All the President’s Men (I concur with narrator Samuel L. Jackson, great movie), with SNL alum Beck Bennett as Woodward and David as a very unhelpful Deep Throat.

After that, Ike Barinholtz, who you’ve seen star in everything from The Mindy Project to History of the World, Part II to The Studio, takes on the role of the deeply antisemitic Henry Ford, who isn’t thrilled to be showing off his new horseless carriage to the local rabbi (David).

The next sketch is devoted to 15th President James Buchanan and his passion for passed apps as well as the ladies. Playing Buchanan’s assistant John Appleton is the very funny Diallo Riddle… Well, you don’t get much of a taste for his talents here, since he’s in straight man mode, but check out the shows South Side (streaming on HBO Max) and the delightful Sherman’s Showcase ( Hulu ), which he co-created and starred in.

At this fancy party, Buchanan proceeds to schmooze a collection of ladies, the first of whom (in the green dress) is played by Jordana Brewster, best known as Dominic Torretto’s little sister Mia in the Fast & Furious movies, but who also made a very funny guest appearance as herself in the second season of The Other Two . Next is Katie Aselton as the waitress Buchanan harasses, in addition to being a big part of the mumblecore indie film scene, she of course worked for years with Pursuit of Unhappiness co-creator Jeff Schaffer on FX’s The League , and is also a director in her own right .

Following Aselton (in the bronze dress) is Merle Dandridge, an incredibly accomplished Broadway actress who also has two notable video game roles to her credit: Alyx Vance in the Half-Life series and Marlene in The Last of Us (a role she actually reprised for the actual TV series). And then the final lady given the opportunity to put Buchanan in his place is played by Andrea Savage, a prolific TV guest star who also has starring roles in Tulsa King and the comedy series I’m Sorry (which she also created). Capping things off is comedian Rory Scovel wielding his homegrown Southern accent as Jefferson Davis, Scovel co-starred with Amy Schumer in the rom-com I Feel Pretty and was a series regular on the Apple TV show Physical .

The episode wraps up with David as the mother of Jonas Salk, bragging on her son to her neighbor Evelyn. Judy Gold has been doing comedy for decades, a true stand-up icon with numerous memorable guest-starring roles on her IMDB . Shockingly, she never guest-starred on Curb , but more than makes up for it here. Playing a gentleman named Bobby who bears no resemblance whatsoever to any members of the current administration’s cabinet is Gregg Perrie, whose credits include Mad Men , House of Lies , and three episodes of Terminator: The Sarah Connor Chronicles .

This episode keeps things relatively tight, largely focused on the assassination of Abraham Lincoln and ensuing aftermath. First, though, the show takes a stop by the OK Corral (at least adjacent to it) for one of the most blindingly obvious casting choices of all time: Timothy Olyphant? As a Wild West gunslinger? Innovative! The Deadwood / Justified / Mandalorian guest star is specifically playing Wyatt Earp, with Don Johnson also starring as Doc Holiday, Johnson has fewer Westerns on his resume than you’d expect, but the Miami Vice favorite does fit naturally into this world.

The supporting cast of that sketch is filled out by Marc Menchaca as the cowboy incensed by David’s character’s “pig-parking” job (his past projects include Dutton Ranch , Ozark , and playing “Klansman Joe” on Curb ), Johnno Wilson as Virgil Earp (also featured in I Love That for You and Twisted Metal ), and Maximo Salas (familiar from shows including Rooster and RJ Decker ).

Then, it’s onto the Lincoln mega-sketch, which features a pitch-perfect casting choice in Bill Hader, who did previously play the 16th President in an SNL sketch. Also perfect casting? Kathryn Hahn as the temperamental Mary Todd Lincoln, it’s always really fun to watch David go toe-to-toe with a comedic actress of his caliber, and the WandaVision / The Studio star is more than up to the task.

Meanwhile, blink and you’ll miss Lennon Parham as one of the actors in Our American Cousin , the play Lincoln was attending the night of his assassination. Parham is a queen of dry delivery, with memorable roles in shows like Minx , Veep , and the charming USA Network series Playing House , which would be great to see available on streaming someday.

The infamous John Wilkes Booth is played by Jay Renshaw, who’s made appearances on The Comeback , The Brothers Sun , and Dead to Me , while Vice President-turned-President Andrew Johnson is played by Seth Morris, a reliable comedy guest star featured on It’s Always Sunny in Philadelphia , Parks and Rec , Happy Endings (Scotty!), and The League . Oh and Curb, just like almost everyone else here.

This episode begins with a real showcase for the talents of Isla Fisher as the wife of Larry’s returning barrel-maker, who (shockingly) gets into a shouting match with Larry over the impending British invasion. Her many past projects include Wedding Crashers , Jay Kelly , and being an original Horseman in the Now You See Me movies. Stepping in as Paul Revere is SNL alum Kyle Mooney, his recent Netflix special Saturday Morning All Star Hits! was a true retro delight.

In a nice bit of race-blind casting, the one and only Keegan-Michael Key gets enlisted to play Texas revolutionary Davy Crockett, who hides a shameful secret under his raccoon skin cap. On the other side of Davy Crockett’s fight is Oscar Nuñez as General Santa Anna, in case you need me to tell you this, Nuñez is best known for his starring roles in The Office and sister series The Paper .

Following that, Larry ruins a dinner party being thrown by Susan B. Anthony, which gives Curb legend Susie Essman the opportunity to match wits with him once again. (It’s actually a pretty restrained performance from Essman, perhaps out of respect to the feminist icon she’s playing, though she does still get to tell Larry to fuck off.) Playing Susan’s sister is 30 Rock and Unbreakable Kimmy Schmidt star Jane Krakowski) brought him along. and sitting on the other side of Larry is Toby Huss, one of today’s great working character actors. (Just this year, he played multiple roles on King of the Hill and showed up on Widow’s Bay !) Also at the dinner table are two true veterans of comedy: sitcom pro Essence Atkins, and comedian’s comedian Wayne Federman.

The episode’s final sketch is another two-hander with Paul Rudd, an actor whose filmography doesn’t feel necessary to explain, so instead I’ll just link to his incredible 2010 appearance on Tim and Eric Awesome Show, Great Job! . You are not ready for Tayne .

The series finale of the show covers three different centuries of history, beginning with a sketch in which Larry learns an important lesson about trying to kiss women without permission, even if World War II has just officially concluded. Teaching him that lesson is Joe Manganiello, an actor with a rich array of credits stretching back to 2002’s Spider-Man , including his incredibly important work in Magic Mike XXL .

From there, the beloved Fred Melamed, that’s right y’all, Sy Ableman himself, shows up as William Henry Harrison, the first President to die in office. Former MadTV cast member and Curb guest star (of course) Lisa Arch plays Mrs. Harrison (whose first name isn’t mentioned on the show, but it was Anna). When President Harrison gets sick after his inaugural address, Larry makes the chaos of his care even worse, especially as he butts heads with Harrison’s doctor, played by Neil Casey. Casey’s a writer and actor whose face you’ve definitely seen across a slew of comedy projects; just recently, he served as a writer and recurring actor on Widow’s Bay .

Then there’s a Donner Party sketch that doesn’t get too graphic about the cannibalism stuff, thankfully. June Diane Raphael ( Grace and Frankie , tons of other comedy stuff), Vince Vaughn (there isn’t enough time in the world to fully list out all his credits), and Jeff Garlin (um, Curb Your Enthusiasm ? Heard of that show?) appear as the other Donners toughing out the long winter with Larry. Greg Kinnear plays the leader of the troupe who finds the Donners, only to regret asking questions about how they survived.

And finally, you probably recognized the guest star in the last sketch: former President/executive producer Barack Obama plays himself in a sketch mocking the deeply unserious 2014 controversy regarding a tan suit . The sketch is followed by a less fictional Obama delivering one last message of hope for the future… before bantering with Larry some more. And thus concludes Life, Larry, and the Pursuit of Unhappiness . Hopefully, we all learned a lot.

New episodes of Life, Larry, and the Pursuit of Unhappiness debut Fridays at 9:00 p.m. ET on HBO and HBO Max.