HBO is famous for creating some of television’s most critically-lauded and groundbreaking programs, with its hilarious comedies being no exception. The premium cable network has been delivering captivating content for the small screen for decades, providing audiences all across the world with endless entertainment. Some of Hollywood’s most dynamic and diverse performers have had a hand in sidesplitting comedies on HBO, firmly establishing the platform as a leading force in the comedy genre. From Ricky Gervais to Sacha Baron Cohen, Danny McBride to Issa Rae, the network has a brilliant way of utilizing its tremendously talented stars.
Updated April 13th 2023: Great news for HBO comedy fans! We’ve updated this article with fresh entries.
Since its debut in 2000, the improvisational comedy Curb Your Enthusiasm has amassed a passionate cult following, with creator and lead actor Larry David engrossing viewers with his self-centered parody of himself. Julia Louis-Dreyfus won six consecutive Primetime Emmy Awards for her dazzling portrayal of the fictional Vice President of the United States Selina Meyer in the political satire smash hit Veep, further demonstrating her exceptional skills. These are 15 of the funniest HBO shows of all time in no particular order, all available on HBO Max.
The Larry Sanders Show
Actor and comedian Garry Shandling co-created and starred in the critically-acclaimed ’90s sitcom The Larry Sanders Show, which provides a hilarious behind-the-scenes look at the eponymous late night talk show host’s interactions with the program’s colorful guests, producers, and crew. Having ran for six lauded seasons from 1992 to 1998, the trailblazing comedy touted an impressive cast including Jeffrey Tambor, Rip Torn, and a young Bob Odenkirk, and featured popular celebrities portraying exaggerated versions of themselves.
The Larry Sanders Show is widely regarded as a landmark television series and during its tenure was the recipient of numerous accolades including three Primetime Emmy Awards, two Peabody Awards and a BAFTA Award.
Veep
Seasoned television superstar Julia Louis-Dreyfus headlined the political satire comedy series Veep, in which she appeared as the fictional Vice President of the United States Selina Meyer, depicting the savvy and charismatic leader’s efforts to make a positive change and create an inspiring legacy for her administration. Like its creators other series, the British comedy The Thick of It, Veep skewers politics and narcissism with acidic wit.
Throughout its seven seasons, Veep provided audiences with a hilariously cynical representation of Washington politics, and showcased sidesplitting, profane performances by its talented supporting cast like Anna Chlumsky, Tony Hale, and Matt Walsh. Upon the completion of its final season, Glamour declared that the award-winning show “should be remembered as one of the best ensemble casts ever, with Louis-Dreyfus surrounded by an absolute murderer’s row of comedic talent.”
The Righteous Gemstones
The Righteous Gemstones is Danny McBride’s third HBO comedy series, following Eastbound & Down and Vice Principals, that will keep you entertained for hours on end. The series follows the chaotic steps of a hugely wealthy, highly corrupt family of megachurch pastors and televangelists led by patriarch Eli Gemstone (played by John Goodman).
Comparing characters of The Righteous Gemstones to The Sopranos, The Guardian quips that the show is what would happen if the infamous mob boss swapped out his gangster lifestyle for the tacky world of megachurches. The Righteous Gemstones was renewed for a third season at the end of 2022, much to the excitement of its dedicated fans.
Barry
Combining thrills and laugh into an unforgettable blend, the critically acclaimed and Emmy-award-winning series Barry (2018-2023) chronicles the bizarre journey of a depressed hitman, Barry Berkman (played by Bill Hader), who travels to Los Angeles to eliminate his latest target.
However, he unexpectedly stumbles upon a newfound passion: acting. As the show progresses through each season, it takes audiences on an exhilarating ride into increasingly darker and more intense themes. But if you like darkly hilarious black comedies, Barry is the perfect series for you.
The Rehearsal
Enter the hilarious and cringe-worthy world of comedian Nathan Fielder in The Rehearsal (2022 – present), a docu-comedy series that showcases Fielder’s incredible talent for turning any situation into the most awkward encounter imaginable. This HBO series features the comedian helping ordinary people to prepare for life’s challenges through carefully crafted simulations. Because why take unnecessary risks when you can take control and shape your destiny?
The Rehearsal is a breath of fresh air in the television world, pushing boundaries with its creative approach. With HBO having already announced The Rehearsal‘s second season, viewers are left to wonder where this one-of-a-kind social experiment will go next.
Mr. Show with Bob and David
The brilliant Bob Odenkirk and David Cross co-created and starred in the 1995 sketch comedy series Mr. Show with Bob and David, in which the two funnymen portray somewhat fictionalized versions of themselves while taking the stage and performing entertaining sketches for a live studio audience. Having previously worked alongside one another in the sketch program The Ben Stiller Show, Odenkirk and Cross began doing comedy routines at clubs after discovering their humor and comedy styles were similar.
During its four seasons, Mr. Show with Bob and David utilized the talent of revered comedians like Sarah Silverman, Jack Black, and Tom Kenny (the voice of SpongeBob), and while it never obtained a mass audience, it has since been heralded as an extremely influential sketch comedy series.
Eastbound & Down
The delightfully rude and crude Danny McBride appears as the self-destructive former major league baseball player Kenny Powers in the sports comedy series Eastbound & Down, which follows the washed-up athlete as he is forced to return to his hometown and teach P.E at his old middle school. Despite his humbling circumstances, Powers is determined to reclaim his fame no matter the cost; beginning the series as a hilariously awful scumbag, the character actually grows a bit and the show evolves as it goes along.
Drawing inspiration from former Major League Baseball players John Rocker and Mitch ‘Wild Thing’ Williams, McBride has since expressed that the tone of Eastbound & Down was intended to “make fun of a South where you could learn an ancient martial art like Tae Kwon Do in a shopping center next to a tanning salon.”
Curb Your Enthusiasm
Written, created by, and starring Larry David of Seinfeld fame, the 2000 sitcom Curb Your Enthusiasm centers on the semi-fictionalized life of the renowned comedian and depicts his amusing everyday interactions with his close friends, acquaintances and passing strangers that are often complicated by David’s own stubbornness, annoyances, and unorthodox approach to socializing.
The TV legend is surrounded by a comically talented supporting cast including Cheryl Hines, Jeff Garlin, Susie Essman, and J.B. Smoove, and the program has garnered universal acclaim for its sharp writing and outstanding improvisational comedy by the actors. Curb Your Enthusiasm is revered for its self-deprecating humor and outrageous performances, and in 2016 was ranked by Rolling Stone as the 19th greatest television show ever made, and has no plans to stop anytime soon.
The Comeback
Friends darling Lisa Kudrow delivered a tour de force performance as Valerie Cherish in the 2005 comedy-drama The Comeback, portraying the floundering B-list sitcom actress who desperately wants to revive her career and agrees to appear in the eponymous reality television show in hopes of elevating her status.
Created by Kudrow and Sex and the City writer/director Michael Patrick King, the series and character Valerie is an extension of a persona she conceptualized while doing improvisational comedy with The Groundlings, naming her “your favorite actress on a talkshow.”
After an initial cancellation following its first season, The Comeback returned to HBO for a critically acclaimed second season in 2014, earning Kudrow the Dorian Award for Best TV Performance of the Year by an Actress for her hilarious work in the revival. An insightful, boundary-pushing comedy with a surprising dose of sadness and bitterness, the show remains a beloved cult favorite with an incredible ending.
A Black Lady Sketch Show
Widely regarded as the first sketch comedy series written, produced and starring Black women, A Black Lady Sketch Show was created by Robin Thede and features the comedian along with fellow actors like Ashley Nicole Black and Gabrielle Dennis as they perform sketches tackling socially relevant themes such as dating, religion and sex.
Hailed for its brilliant blend of absurdity and playfulness, the program was a smash-hit among critics, earning a perfect Rotten Tomatoes score and winning three Black Reel Awards and a TCA Award. Salon called the comedy series “a blend of nuanced observations about the systemic invisibilities and challenges of women of color and sidesplitting sketch premises.”
Da Ali G Show
Having first made its debut in the UK on Channel 4, the satirical television series Da Ali G Show called HBO its home for the following two seasons, with the raunchy program starring Sacha Baron Cohen as three unconventional personas: the wannabe rapper Ali G, flamboyant Austrian fashion reporter Brüno Gehard, and the misogynistic but affable Kazakhstani reporter Borat Sagdiyev.
Baron Cohen delivered a genius satirization of political and pop culture journalism, conducting real interviews with unsuspecting famous figures and faces, captured through hidden cameras. Da Ali G Show caused quite the controversy during its run, but nonetheless featured an iconic and uproarious performance by Baron Cohen, and would lead to the hit films Brüno, Borat, and its sequel.
Silicon Valley
Chronicling the ups and downs of the startup company Pied Piper and the lives of those who conceptualized it, the 2014 comedy series Silicon Valley stars Thomas Middleditch as the business’ introverted computer programmer and founder Richard Hendricks as he tries to make it rich with his brainy buddies.
Co-Created by Beavis and Butt-Head mastermind Mike Judge, the program was inspired by the TV vet’s own experience at a Silicon Valley startup in the 1980s and his disdain for the culture and his colleagues at the company. Silicon Valley was critically lauded during its 6 season tenure for its savvy and entertaining insight into the tech world, winning numerous accolades like Satellite Awards and Critics’ Choice Television Awards.
Insecure
The always charming Issa Rae co-created and starred in the 2016 comedy-drama Insecure, which follows longtime best friends Issa (Rae) and Molly (Yvonne Orji) as they attempt to navigate their personal relationships and career aspirations while living in Los Angeles. The series also depicts the characters as they endure amusingly awkward and uncomfortable everyday situations, as told through the perspective of contemporary African-American women.
Prior to the show’s premiere, Rae told Los Angeles Times that Insecure will delve into “the complexities of ‘Blackness’ and the reality that you can’t escape being black” while elaborating that, “We’re just trying to convey that people of color are relatable. This is not a hood story. This is about regular people living life.”
The Kids in the Hall
The 1988 Canadian sketch comedy series The Kids in the Hall centers on the eponymous comedy troupe featuring brilliant comedians Dave Foley, Mark McKinney, Scott Thompson, Kevin McDonald and Bruce McCulloch as they perform surreal and amusing skits reminiscent of Monty Python’s Flying Circus. The cast members frequently dressed up in drag for their quirky characters and opted to appear as themselves as opposed to impersonating celebrities and pop culture moments.
The program had immense success during its six seasons and went on to inspire future comedy writers and performers like the creators of Portlandia and South Park, along with a generation of LGBTQ+ comedians. A successful revival of Kids in the Hall premiered on Amazon Prime Video in 2022 with the original cast.
HBO
The 2005 British sitcom Extras was directed, created, and written by Ricky Gervais, with the English comedian also leading the series that centered on the extras working on various television, film, and theater projects. In the playful and engrossing satire, Gervais portrays background performer Andy Millman, showcasing the extra’s work as he attempts to find bigger roles and opportunities in the entertainment industry.
Hollywood superstars like Ben Stiller, Kate Winslet, Samuel L. Jackson, and many more also made appearances on the cheeky program, which ran for two seasons and was followed up with a Christmas special. Extras was well-received by critics during its short but impactful run, with the Sydney Morning Herald writing, “It’s the comedy of awkward moments, of embarrassing pauses, of the wrong thing said at the wrong time, of people being caught out doing things behind somebody’s back. It’s painful to watch – and ceaselessly funny.”
