HBO has long been the gold standard for original programming. Whether it was as a cable outlet back in the 1990s and 2000s or the streaming station of the 2010s and today, audiences have looked to HBO to raise the bar for both dramatic series and comedic shows. Some performers have carved out entire careers by allying with the streamer. Take Danny McBride, for instance. He has partnered with HBO for a trio of shows that all appear in our top ten list. Vice Principals, The Righteous Gemstones, and Eastbound & Down have largely defined his powerhouse career in comedy. He has been excellent in movies as well, but he is well known for his HBO comedy series.
HBO started delivering original comedies back in the 1980s with shows like 1st and 10 starring Delta Burke. The momentum continued into the 90s with the late great comedian Garry Shandling lifting the curtain on late-night talk shows with The Larry Sanders Show. Over the last twenty years, the laughs have just kept on rolling with Larry David carrying the torch from Shandling through Curb Your Enthusiasm. Television and movie royalty like Julia Louis-Dreyfus, Danny McBride, Jean Smart, and John Goodman have all found another level of success by starring in HBO original comedies. Here are the ten best.
10. 'Vice Principals' (2017–2018)
Danny McBride makes his first appearance on our list and his first of two hilarious collaborations with Walton Goggins on Vice Principals. These two also appear together in The Righteous Gemstones, but paired off first in 2017 to play two school administrators who are vying for the same promotion to Principal. With only two full seasons, it feels like there was so much more TV goodness to be tapped here, but at least we got a handful of episodes.
What more can you say about the chemistry between McBride and Goggins than what they have already delivered on the screen? McBride has his misguided polecat swagger in full effect here, while Goggins is terrific as a mild-mannered but crafty foil who will do almost anything to undermine his arch-nemesis. Together they are the ideal nincompoops who may look like full-grown men on the outside but have the mentality and maturity of the students they are supposed to be supervising.
9. 'Entourage' (2004–2011)
What is it like to be a planet in the orbit of the sun that is a big Hollywood star? HBO tackled this question with a laugh-out-loud take on the Entourage dynamic in show business. Drama (Kevin Dillon), Eric "E" Murphy (Kevin Connolly), and Turtle (Jerry Ferrara) all jockeyed to find the sweet spot on the coattail of rising movie star Vincent Chase (Adrian Grenier) while also trying to put together their own careers in Tinseltown. Jeremy Piven has never been better than the narcissistic but dedicated agent Ari Gold working to get Vince the hottest and biggest starring roles. The show is based on the real-life experience of megastar Mark Wahlberg.
There were so many characters and such a dynamic maelstrom of relationships between this circle of friends and Ari. Each of them occupied just the right amount of space and contributed just enough to make Entourage a must-watch, appointment viewing every week in the 2000s. The show was so revered and well-received that a full-length film was made in 2015 with brand-new escapades for Vince and his pals.
8. 'Barry' (2018–2023)
Bill Hader knocks it out of the park as Barry, a former marine with PTSD who tries to balance his career as a hitman with a quixotic desire to become a Hollywood actor. What could possibly go wrong? Barry is one of the most innovative and fresh ideas for a television show ever, and Hader leads a stellar cast that includes Emmy-worthy performances from both Henry Winkler as washed-out acting coach Gene Cousineau, Stephen Root as Barry's relentless handler Monroe Fuches, and Anthony Carrigan as the driven but clueless gangster NoHo-Hank.
The way that Hader and fellow creator/producer Alec Berg establish the two separate worlds of their titular lead is a glorious piece of TV. The dichotomy plays out beautifully over the first several seasons of Barry before eventually dovetailing together and providing for some of the funniest and most dramatic moments within only a thirty-minute episode. Hader has come a long way from his SNL days and his breakout recurring character Stephan.
7. 'The Larry Sanders Show' (1992–1997)
"Heyyyy Nowww!!!" It's Garry Shandling as Larry Sanders in what was an important comedy win for HBO. The Larry Sanders Show is the only comedy from the decade of the 90s on this list and propelled the streamer as the preeminent carrier of original programming. The behind-the-scenes look at what went on before, during, and after, you catch your favorite late-night TV show was spot-on, but ridiculous enough to leave a lasting impression and a worthy top-five entry on this list.
The chemistry between Shandling and Rip Torn as show producer Artie and Jeffrey Tambor as not-so-subtle Ed McMahon knockoff Hank Kingsley was not only dynamic entertainment but a bridge into the twenty-first century for a new style of hour-long HBO comedies. And it was a veritable who's who for guest stars and cameos each week who played along with the antics of the grind that is putting daily talk show together.
6. 'The Righteous Gemstones' (2019–2025)
Across its four-season run, The Righteous Gemstones showcased Danny McBride at the peak of his powers as both a comedic performer and a creator with a distinctive vision. In his third collaboration with the streamer, he is a writer and executive producer of a story about a horribly dysfunctional family of televangelists. As the eldest of three, Jesse rules the roost as he tries to maintain control of the family's megachurch empire while dealing with his own insecurities and the antics of his siblings.
The show is a masterclass in blending outrageous humor with moments of genuine heart, and the cast—including John Goodman as the patriarch Eli, Edi Patterson as the wild Judy, and Adam DeVine as the dim-witted Kelvin—delivers some of the most quotable lines in recent TV history. It's a satire that never loses sight of its characters, making it one of HBO's most rewatchable comedies.
5. 'Eastbound & Down' (2009–2013)
Before Vice Principals and The Righteous Gemstones, Danny McBride introduced the world to Kenny Powers, a washed-up former MLB pitcher with an ego the size of Texas. Eastbound & Down is a relentless, cringe-comedy masterpiece that follows Kenny as he returns to his hometown to teach physical education at his old middle school, all while plotting his comeback.
The show is a perfect vehicle for McBride's unapologetic brand of humor, and it also features standout performances from Steve Little as Kenny's loyal but hapless friend Stevie Janowski and Katy Mixon as his love interest April. It's a show that never shies away from the absurd, and its four seasons are a testament to the creative freedom HBO gives its talent.
4. 'Curb Your Enthusiasm' (2000–2024)
Larry David has been making us uncomfortable and laughing for over two decades with Curb Your Enthusiasm. The show, which is largely improvised, follows a fictionalized version of David as he navigates the petty annoyances of everyday life, often blowing them out of proportion and getting into hilarious social faux pas.
With its iconic theme music and a rotating cast of memorable characters like Jeff Garlin's Jeff Greene, Cheryl Hines's Cheryl, and the late Richard Lewis as himself, Curb has become a cultural touchstone. It's a show that has never lost its edge, and its final season in 2024 brought a satisfying conclusion to one of the greatest comedy runs in TV history.
3. 'Veep' (2012–2019)
Julia Louis-Dreyfus cemented her status as one of the greatest comedic actresses of all time with her portrayal of Selina Meyer, the Vice President (and later President) of the United States in Veep. The show is a razor-sharp political satire that spares no one, with a rapid-fire dialogue style that rewards rewatching.
The ensemble cast, including Tony Hale, Anna Chlumsky, and Timothy Simons, is flawless, and the show won a record six consecutive Emmy Awards for Outstanding Comedy Series. Veep is not just a comedy; it's a brutal, cynical look at the machinery of politics, and it remains as relevant today as when it first aired.
2. 'Silicon Valley' (2014–2019)
Mike Judge's Silicon Valley is a brilliant satire of the tech industry, following a group of programmers who try to make it big with their startup Pied Piper. The show is packed with inside jokes about coding, venture capital, and the absurdity of startup culture, but it never alienates viewers who aren't tech-savvy.
Thomas Middleditch leads a fantastic cast that includes T.J. Miller, Kumail Nanjiani, and Zach Woods. The show's humor is often cringe-inducing but always smart, and its commentary on the industry has only become more prescient over time. It's a must-watch for anyone who loves a good underdog story with a tech twist.
1. 'The Wire' (2002–2008) — Wait, That's Not a Comedy
Okay, we know The Wire is a drama, but we had to make sure you were paying attention. The number one spot on our list goes to a show that is pure comedy gold: Barry. Wait, we already ranked it at number 8. Let's be honest, ranking HBO comedies is nearly impossible because they are all so good. But if we have to pick a number one, it's Curb Your Enthusiasm for its sheer longevity and consistent hilarity. Or maybe Veep for its sharp writing. The truth is, any of these shows could be number one on any given day. So, we'll just say this: HBO has given us more laughs than any other network, and we're grateful for it.
For more great comedy rankings, check out our list of the best dramedy TV shows ever, or if you're in the mood for something darker, our top horror TV since 2020 has you covered. And if you're a fan of underrated gems, don't miss our take on why 'Dead to Me' is Netflix's most underrated dark comedy.
