HBO is America’s first cable-originated television content service and one of the oldest subscription television services in the United States. It proved that an entire television empire could be funded solely through direct subscriber fees rather than commercial advertising in the early ’70s. From groundbreaking prestige dramas to laugh-out-loud original comedies, it has consistently stayed ahead of the curve, delivering first-class entertainment for more than 50 years.
I grew up obsessed with the network’s output in the ’90s and ’00s, and I was also raised on the TV shows my dad had grown up with and collected on VHS. In our household, it wasn’t unusual to watch Tales from the Crypt, then put on Sex and the City, and then go straight into an episode of Def Comedy Jam. More recently, I’ve come to appreciate how, freed from broadcast censors and the demands of advertisers, the network was able to invest in cinematic production values, complex antihero narratives, and serialized storytelling. It kickstarted a new era of prestige television, beginning with trailblazing hits such as Oz, The Wire, and The Sopranos.
Why You Should Trust Me: I’m an avid fan of cinema and television and have been writing for MovieWeb for five years. I was raised on so much television that I instinctively wait for a studio audience to laugh every time I make a mildly amusing comment in real life. Over the years, I have made a concerted effort to explore pretty much everything the medium has to offer, encountering the fantastic, the middling, and the outright awful. As a result, my expertise in all things television will hopefully help you avoid the latter and experience only the finest HBO shows.
Honorable Mentions
‘Fraggle Rock’ (1983 – 1987) – Created by the team who gave us The Muppets and Sesame Street, Fraggle Rock was a puppet-based, musical children’s show. It’s charming, fun and full of heart. However, I didn’t pick it for the main list because, compared to the aforementioned Jim Henson classics, it falls short in terms of sheer legendary status.
‘Sex and the City’ (1998 – 2004) – Admittedly, when you peel back the glossy surface of Sex and the City, it’s easy to see why so many people argue that it’s somewhat problematic. Working against modern ideas of feminism, the show often ties female empowerment to consumerism, glamorizes unhealthy relationship dynamics, and sometimes reduces independence to buying shoes or chasing Mr. Big. These critiques aside, it’s an undeniably entertaining, uber-addictive work of champagne-soaked escapism that won the hearts of millions of viewers around the globe. It became one of HBO’s most successful shows of all time.
‘Oz’ (1997 – 2003)
A Brutal Prison Drama That Changed TV Forever
Watch This If: You want to witness a truly groundbreaking piece of hard-hitting television. Oz is set in a fictional men’s prison, and it was the first one-hour dramatic television series produced by HBO. It explores the brutal, interconnected lives of its inmates. It is also arguably the first ever show to be considered “prestige television,” a term coined to describe the new wave of high-quality programming that combined cinematic production values with complex characters and deep, compelling storytelling.
Skip This If: You have a weak stomach. Aiming to realistically portray life in a maximum security prison, Oz is relentlessly violent and features many graphic scenes. Free from broadcast censors, it pulls no punches. Even to this day, its visceral violence and bleak tone land it among the most disturbing shows ever aired on HBO.
‘True Detective’ (2014 – Present)
A Slew of Talented Hollywood A-Listers Star in This Dark and Gritty Detective Series
Watch This If: You’re looking for a gritty crime thriller with soaring cinematic execution and A-list actors. Blending crime drama with psychological thrills, Hollywood heavyweights including Matthew McConaughey, Woody Harrelson, Colin Farrell, Rachel McAdams, Mahershala Ali, and Stephen Dorff are dropped into a world of dread and corruption as we explore a series of horrendous crimes and the ensuing investigations. Leaning heavily into Southern Gothic with neo-noir tropes, True Detective is bleak and morally ambiguous but endlessly entertaining and masterfully executed.
Skip This If: Cozy, easy-to-follow murder mysteries, in the vein of Only Murders in the Building, are your idea of a perfect night in. Focusing heavily on atmosphere and tone, True Detective is often told through a non-linear narrative. It avoids traditional mystery clichés and tropes by revealing key pieces of information later in the story. That completely changes how events are perceived, keeping viewers on their toes and making it one of the most unpredictable and exciting shows in recent history.
‘Def Comedy Jam’ (1989 – 1997)
Hilarious, Raw and Unfiltered Stand-Up Comedy From The Best in The Biz
Watch This If: Like me, you like your comedy raw and unfiltered and are looking to witness early career stand-up sets from some of the world’s biggest comedians including Dave Chappelle, Chris Rock, Jamie Foxx, Bill Burr, and Chris Tucker. Bypassing mainstream television gatekeepers, Def Comedy Jam allowed its guests to share their authentic cultural perspectives without mainstream sanitization.
Skip This If: You want to watch it with your kids. Much of the humor is rude, crude, and, at times, utterly outrageous. Full of X-rated content, some of the most notorious performances include Bernie Mac’s explicit routine and Martin Lawrence’s brutal crowd roasting.
‘Boardwalk Empire’ (2010 – 2014)
A Prohibition-Era Gangster Show Featuring a Superb Performance From Steve Buscemi
Watch This If: You’re interested in the Prohibition era and the organized crime that ran rampant at the time. Based on real gangsters like Al Capone as well as its own fictional characters, Boardwalk Empire is a compelling crime drama set during one of America’s most fascinating time periods. Superb acting from the likes of Steve Buscemi and Michael Pitt, combined with meticulously detailed costume designs and evocative cinematography, make it a must-see for any gangster crime fan.
Skip This If: You’re a stickler for historical accuracy looking for a purely fact-based, true-crime thriller. While the show features many real events, characters, and settings, it plays fast and loose with the facts. It also takes a fair amount of creative liberties, creating new characters and subplots. It’s more an exploration of the era’s atmosphere over a documentary-style retelling of specific events.
‘Tales From the Crypt’ (1989 –1996)
An Anthology Horror Series That Pushed Boundaries
Watch This If: Your interest is piqued at the notion of discovering one of the most groundbreaking horror shows of all time. Tales from the Crypt has firmly cemented its place in popular culture, and while many certainly remember the show’s wisecracking Cryptkeeper puppet host, what some may not quite remember is just how terrifying some of those episodes were. While it was clearly influenced by fellow horror/mystery anthology show The Twilight Zone, HBO didn’t have to adhere to the censorship standards of most networks. As a result, HBO allowed the series to include content that had rarely appeared on television up to that time, including graphic violence, profanity, and sexual activity.
Skip This If: You’re looking for deep, multi-episode story arcs and evolving character dynamics. Tales From the Crypt is an anthology series, and each episode features a self-contained story. Its episodes range from campy and comedic to genuinely chilling, which keeps it fresh and entertaining. However, it might not be for those who prefer deep continuity over quick, standalone thrills.
‘Game of Thrones’ (2011 – 2019)
This Work of High Fantasy is One of the Most Critically Acclaimed Shows of all Time
Watch This If: You want the Citizen Kane of fantasy television. Game of Thrones is one of the most popular and critically acclaimed shows of all time, with a staggering 59 Primetime Emmy Awards under its belt, the most of any scripted series. Based on George R.R. Martin’s A Song of Ice and Fire novels, it takes the sweeping, high fantasy grandeur of The Lord of the Rings and makes it a little grittier and bloodthirsty.
Skip This If: You prefer your television experiences to be relatable or grounded in reality. Game of Thrones is a pretty “high fantasy” affair that takes place in an entirely fictional world with its own geography, history, and rules. There are dragons, resurrections, and plenty of magical moments. However, it still retains a sense of gritty realism as it explores politics, warfare, social structures, and the day-to-day lives of its characters. Just don’t expect any courtroom drama or forensic investigations.
‘Curb Your Enthusiasm’ (2000 – 2024)
Cringe Comedy at its Finest
Watch This If: You have ever wondered what would happen if you always said exactly what was on your mind instead of being so polite. Curb Your Enthusiasm’s Larry David is as cynical as they come and utterly unfiltered. His inability to keep his thoughts to himself lands him in a series of hilarious situations, which are heightened by his social awkwardness. The HBO show is smart, irreverent, and highly influential.
Skip This If: You prefer a show with a clear-cut, likable protagonist, or you find that “cringe humor” leads to intense physical discomfort. The show’s brand of cringe comedy, which derives its humor from socially awkward situations and second-hand embarrassment, thrives on Larry’s unhealthy pleasure in exploiting this discomfort. Petty and stubborn, he refuses to conform to social norms and often escalates minor personal grudges into major conflicts, leaving chaos in his wake.
‘The Wire’ (2002 – 2008)
A Gritty, Ultra-Realistic Exploration of Urban Decay in Baltimore
Watch This If: You want to experience the very best the crime drama genre has to offer. Universally acclaimed, The Wire was written by former police reporter David Simon and former homicide detective and public school teacher Ed Burns. They drew from their real-life experiences to create one of the most hard-hitting, realistic depictions of urban decay ever committed to the screen. The series is told from the perspectives of both the police and the criminals. The gritty, immersive, and cynical picture they paint of the Maryland city makes for a compelling crime drama.
Skip This If: You want instant gratification. From the get-go, The Wire drops viewers into the gritty, urban streets of Baltimore with little to no exposition. The frequent police jargon and street slang are complex and alien to most and take some time. Additionally, some might find the pacing too slow and might feel frustrated waiting for the action.
‘The Sopranos’ (1999 – 2007)
A Ground-Breaking Gangster Show That’s Regarded as One of the Greatest Shows of All Time
Watch This If: You want to find the show that redefined what “prestige television” looked like and influenced countless shows in its wake. The Sopranos proved that TV could rival cinema in quality and ambition. A gangster crime series at its core, it incorporates elements of family drama, surrealism, and dark comedy, with a strong focus on mental health. Through Tony’s therapy sessions, the show explores the emotional toll that a life of crime has taken on its complex and layered anti-hero lead. Masterfully acted, sharply written, and immaculately directed, The Sopranos‘ bold storytelling, rich character development, and brooding atmosphere set the benchmark for the genre and helped usher in a new “golden age” of TV.
Skip This If: You plan to binge the entire show and are put off by repetitive story structures. It’s been argued that as the show progressed, certain aspects of the story became somewhat formulaic, relying on a loop where a new capo or associate causes trouble and gets killed.
