The Best HBO Comedies From ‘Barry’ to ‘Veep’

HBO may be more well-known for its numerous drama series—Game of Thrones, The Wire, and The Sopranos, perhaps being the most well-known examples—but the network also boasts a fantastic and incredibly diverse range of original comedy series as well.

Most recently, the newest addition to the long list of HBO comedies, Peacemaker, has officially wrapped its first season on HBO Max. Though having just concluded its initial season, Peacemaker ​​earned significantly positive reviews from critics, casual viewers, and fans of the superhero genre, with the series’ finale setting the record for the highest single-day streaming viewership for an HBO Max original episode.

With Peacemaker having just ended, we thought we’d take a look back at some of the greatest comedy series ever to premiere on HBO that you could binge right now on the streaming platform.

High Maintenance

high maintence
Courtesy of HBO Max

One of the most underrated shows to probably ever exist, High Maintenance is a unique “day in the life” style anthology series providing a snapshot for literally dozens of New Yorkers, each with their own complex problems and eccentric lifestyles.

At the heart of the series, High Maintenance focuses on a cannabis dealer (known only as “the Guy”—as in “my weed guy”—played by series co-creator Ben Sinclair) and the various clients he deals to. However, rather than being strictly about the Guy and his weekly misadventures, High Maintenance instead provides small, in-depth looks into the lives of his many clients.

It’s an incredibly clever premise that the show’s creators use to tell stories of the many diverse residents of New York City, with no two single characters or their stories even remotely resembling one another’s.

Praised by numerous critics, the show has been lauded for its sensitivity, humor, and inclusiveness in terms of ethnic diversity.

Two episodes from Season 1—“Meth(od) and “Grandpa”—were selected on several publications’ lists for “The 25 Best TV Episodes of 2016, with Season 2’s “Globo” named by Time and Variety as one of the “Best TV Episodes of 2018.”

Flight of the Conchords

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Courtesy of HBO Max

There’s a ridiculous amount of HBO series featuring actors playing fictionalized versions of themselves. You don’t have to look much farther than the guests on The Larry Sanders Show or Curb Your Enthusiasm to see evidence of that fact. Somewhat lesser known than those two shows is Flight of the Conchords, the light-hearted musical sitcom starring the real-life New Zealand musical duo of the same name, composed of members Bret McKenzie and Jemaine Clement.

In this series, McKenzie and Clement play caricatured versions of themselves, presented as a struggling musical act from New Zealand seeking fame, fortune, and love in New York City, almost inevitably failing to find all three in the course of each episode.

Characterized by its deadpan humor and spontaneous musical numbers, Flight of the Conchords was very positively received from critics, earning 10 Emmy nominations, including “Outstanding Comedy Series” and “Outstanding Lead Actor in a Comedy Series” (Clement).

Even if the comedic style of the show (somehow) doesn’t hook you, you’ll very likely be won over by the series’ numerous original songs, which range in number from two to three per episode, and are almost always funny or a definite earworm (sometimes even both).

Last Week Tonight With John Oliver

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Courtesy of HBO Max

Initially, it was difficult to decide whether or not to include John Oliver’s adult-oriented, late-night talk show, Last Week Tonight, on a list where the primary entries are story-driven comedy series. Ultimately, though, with how much critical acclaim the show has received since it first aired on HBO in 2014, we realize that it’s nearly impossible not to include it on a list of the network’s most noteworthy comedy shows.

As mentioned above, unlike every other entry on this list, Last Week Tonight does not contain a strict story or formal plot of any kind.

Instead, it’s a talk show in the manner of The Daily Show (where Oliver got his start) and The Colbert Report where British comedian and political commentator John Oliver discusses breaking news stories of high public interest. Often, the subjects discussed by Oliver can be deadly serious—COVID vaccinations, wars, and global and domestic politics—but Oliver’s delivery makes it all equally palpable to hear about as well as being startlingly factual.

For his work on the series, Oliver has won 13 Emmy awards as well as two Peabody awards, and was eventually included in the Time 100 list of Influential People, with reviewers praising him as a comedian unafraid to tackle the weighty subject matter.

Additionally, Oliver has been credited with ushering in new social changes and challenging various industries and political institutions, including aimed attacks against the tobacco industry, China’s government, and even televangelists.

Sex and the City

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Courtesy of HBO Max

Sex and the City may not be the best show to ever premiere on HBO, but it’s certainly one of the most noteworthy. The series’ popularity helped secure a wave of new viewers to HBO back in the late 1990s’ and early 2000s’, helping HBO become a well-known network in the subsequent decade.

Based on Candace Bushnell’s 1994 to ‘96 newspaper column of the same name, Sex and the City follows a group of middle-aged women in New York City who remain close friends over the years, telling each other all about their ever-eventful sex lives.

For its time, Sex and the City was revolutionary, pioneering female-centric narratives that proved stories featuring predominantly women could be every bit as engaging and entertaining as those built around men.

Praised today for its trail-blazing portrayal of femininity, promiscuity, and sexuality, Sex and the City was and continues to be one of the most popular and influential HBO series of all time.

During its initial six season-long run, the series won seven Emmy Awards (including Outstanding Comedy Series), eight Golden Globes, and three Screen Actors Guild Awards. In 2007, Time magazine named it one of the greatest TV shows of all time.

The show’s popularity would later result in two feature-length films, a prequel series on The CW (The Carrie Diaries), and a sequel series titled Just Like That… that premiered on HBO in December, 2021.

Barry

barry
Courtesy of HBO Max

A dark comedy crime series created by Bill Hader and Alec Berg, an executive producer who worked on Curb Your Enthusiasm, Silicon Valley, and Seinfeld? How could that not be good?

Barry stars Hader as the titular character, Barry Berkman, a former Marine turned hitman who ends up finding a place in a Los Angeles acting workshop, and who soon develops dreams of becoming an actor. Hader is no stranger to more dramatic performances—his starring role alongside Kristin Wiig in The Skeleton Twins proves that—but here, he plays a very different sort of character than he’s ever played before.

As Barry, Hader appears as someone in anguish over his violent past both as a soldier and an assassin, and who longs for a change in his life. Finding acceptance for the first time in his life in his acting group, Barry tries to reinvent himself and start fresh, only for elements of his past life—mainly various criminal acquaintances—to prevent that from happening.

Described as a cross between Unforgiven, Grosse Pointe Blank, Waiting for Guffman, and Breaking Bad, the series has received universally positive reviews, with specific acclaim going to the writing and acting (especially Hader’s and his co-star, Henry Winkler’s).

The show earned a total of 30 Primetime Emmy nominations, with Hader winning Outstanding Lead Actor in a Comedy Series twice and Winkler winning Outstanding Supporting Actor in a Comedy Series.

The first episode of Season 3 is set to premiere on April 24.

Silicon Valley

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Courtesy of HBO Max

From co-creator Mike Judge—the man behind Office Space, King of the Hill, and Beavis and Butt-Head—comes this immensely enjoyable satire of Silicon Valley and the modern tech industry.

Richard Hendricks (Thomas Middleditch) is a software coder struggling to ensure his new startup is a success. Basing his company out of a house shared with his fellow employees, Hendricks tries to compete against larger corporate rivals and learn the more pragmatic side of owning and operating a business with his friends.

The brilliance of Silicon Valley is its wonderful depiction of its eponymous setting. In essence, it feels like a typical rags-to-riches story where absolutely everyone has an idea for a technology business or an app, including the person working the register at a grocery store.

However improbable their chances of success might be, Hendricks and his coworkers (TJ Miller, Martin Starr, Kumail Nanjiani, and Zach Woods) navigate the often cutthroat world of Silicon Valley, presenting the tech industry in a comedic, parodic new light.

Critically praised from its initial first season onward, Silicon Valley earned the Primetime Emmy Award nomination for Outstanding Comedy Series five years in a row.

The Larry Sanders Show

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Courtesy of HBO Max

One of the most influential sitcoms of all time, The Larry Sanders Show was simply unlike anything else that was on television in the 1990s’, depicting the day-to-day operations at a fictional late-night talk show.

Co-created by star Garry Shandling and based on his experiences in stand-up and brief stint guest-hosting The Tonight Show, The Larry Sanders Show follows the main cast members of the eponymous talk show in both their personal and professional lives.

Each episode also features hilarious cameos from established celebrities of the time as guests on Sanders’ show, playing satirized versions of themselves. The accolades won by The Larry Sanders Show go on and on. During its original syndication, it won 24 major television awards (including three Primetime Emmys, two Peabodys, and a BAFTA), earning a grand total of 86 nominations from various TV organizations and ceremonies.

Cited as an inspiration on everything from Curb Your Enthusiasm to The Office, it’s been named one of the greatest HBO series of all time, ranking favorably on Time magazine’s list, “The 100 Best TV Shows of All Time,” and placed at number 38 on TV Guide's 50 Greatest TV Shows of All Time.

Veep

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Courtesy of HBO Max

Created by Armando Iannucci as an American adaptation for his British sitcom, The Thick of It, Veep is one of those shows that managed to get better and better over time, eventually becoming one of the most popular and well-received series on HBO in the past decade.

A parody of modern-day politics, Veep is essentially a comedic version of The West Wing, detailing the life of fictional Vice President Selina Meyers (Julia Louis-Dreyfus), an ambitious politician who wants to make a legitimate change in government, but who is almost always thwarted by the trivial day-to-day operations of her position.

Positively received in its first two seasons, by Season 3, Veep had gained serious traction, with critics praising it for its sharp political commentary and hilarious satirical presentation of the US government.

The number of awards Veep was nominated for are practically endless. It would win the Primetime Emmy Award nominations for Outstanding Comedy Series three times, having been nominated in that same category seven years in a row.

In addition to its brilliant writing, Louis-Dreyfus' starring role also earned significant acclaim, resulting in her winning the Primetime Emmy Awards for Outstanding Lead Actress in a Comedy Series for six consecutive years.

Succession

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Courtesy of HBO Max

It’s a tough choice on whether to classify Succession as a comedy or drama, as—like so many HBO series (The White Lotus, High Maintenance, and Barry)—it seems to blur the line between the two. However, because of its primary description as a “dark comedy,” we decided to include it here.

One of the most successful shows on HBO right now, Succession tells the story of the Roys, an extremely wealthy family who own a massive media and entertainment company. After they learn about their patriarch’s (Brian Cox) deteriorating health, the family soon devolves into brutal infighting as they battle for control of their global financial empire.

Like Veep, Succession initially aired to solid positive reviews, but would only improve with each new season. Critics praised the show’s exploration of family, wealth, power, and privilege, as well for the show’s exceptional writing and performances—especially Cox and his co-star Jeremy Strong.

Succession received numerous awards and nominations from virtually every prestigious TV ceremony and organization there is, including the Golden Globe for Best Television Series  (Drama), the Primetime Emmy for Outstanding Drama Series, and the BAFTA for Best International Programme.

Star Brian Cox would also receive a Golden Globe for Best Actor–Television Series (Drama), with Strong winning the Emmy for Outstanding Lead Actor in a Drama Series.

Curb Your Enthusiasm

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Courtesy of HBO Max

One of the best TV shows in HBO history, Curb Your Enthusiasm is a show that will seemingly never get old or stop being funny, coming so far since the release of its pilot in 2000, yet remaining every bit as hilarious as it did 22 years ago. Created by star Larry David, Curb portrays a fictionalized version of David in his post-Seinfeld career. Each episode revolves around his failed, often confrontational interactions with friends, family members, colleagues, and occasionally complete strangers.

After the cultural phenomenon that was Seinfeld forever changed the landscape of television, David pulled off a miraculous second act that seemed like a more mature version of his hit sitcom, depicting the everyday, trivial matters of life in an entirely fresh, endlessly funny way.

The genius of Curb is how well it manages to stay with the times, remaining relevant by including top stars of the day playing exaggerated, egocentric versions of themselves (Ted Danson, Richard Lewis, David Schwimmer, Lin Manuel-Miranda, etc.) as well as lampooning current cultural issues of the day.

It’s for this very reason that fans eagerly await each new season to see what issues the series will tackle, and which new actors will figure into the plot.

Like Seinfeld, it’s a show about nothing and relies heavily on the improvisation of the actors involved, but is arguably every bit as funny as David’s original NBC series.

More From Wealth of Geeks

This post was produced and syndicated by Wealth of Geeks.

Image Credit: HBO Max. 


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Richard Chachowski is a freelance writer based in New Jersey. He loves reading, his dog Tootsie, and pretty much every movie to ever exist (especially Star Wars).