A great show should look different by Season 5. After all, the premise that hooked viewers in Season 1 can’t keep doing the work forever. There are only so many times before familiar conflicts start repeating themselves and characters begin running in circles. The best writers understand that reaching Season 5 should mean something has changed along the way. That can be in the form of character growth, changing relationships, and sometimes, even reworking the central conflict of the story.
That’s easier said than done, but thankfully, HBO has produced several shows that knew exactly what to do with the time they had. None of the five shows on this list ends as a longer version of what it was in Season 1. In fact, they evolve without losing what made them great in the first place, which is exactly why they are considered the greatest.
5
‘Insecure’ (2016–2021)
Insecure is easily one of the most accurate and realistic depictions of adulthood on television. The HBO comedy begins with Issa Dee (Issa Rae) approaching 30, stuck in a job she hates, questioning her long-term relationship with Lawrence (Jay Ellis), and wondering whether everyone around her has life figured out better than she does. Her best friend Molly Carter (Yvonne Orji) appears far more successful on paper, but her dating life and tendency to overthink everything practically reveal a different kind of insecurity. Together, they spend five seasons stumbling through careers, relationships, friendships, and the uncomfortable realization that becoming the person one wants to be usually takes longer than expected.
The most grounded aspect of the show is how Issa doesn’t suddenly discover some bigger purpose after a eureka moment. Instead, the show simply lets time pass as she goes through life’s ebbs and flows. That isn’t to say she doesn’t experience growth — Insecure comes full circle at the end of its five-season run. It doesn’t tie everything up into a neat little bow, but makes the audience realize that perfection was never the point anyway.
4
‘Hacks’ (2021–2026)
Hacks is technically a comedy, but this HBO series captures the full range of the human condition in completely unexpected ways. The show follows legendary Las Vegas comedian Deborah Vance (Jean Smart), whose long-running residency is beginning to look increasingly outdated. On the other hand, Ava Daniels (Hannah Einbinder) is a young comedy writer whose career collapses after an offensive joke leaves her practically unemployable. Deborah needs fresher material, and Ava needs a job, so their manager forces them together. Now, neither of the two ladies is particularly happy about this arrangement, especially since they are total opposites in terms of their approach to life and have a massive generational gap, which adds another layer of tension to the dynamic. However, the show follows the two as their relationship gradually starts changing.
Ava pushes Deborah to make her comedy more honest, while Deborah teaches Ava the ins and outs of an industry where women are rarely given their due respect. The clever part is that Hacks never lets either woman remain comfortably the mentor or student. Deborah and Ava keep butting heads, but they always find their way back to each other. Their conflicts keep Hacks from ever feeling stale, especially since they are always rooted in the characters’ individual journeys. Plenty of comedies can keep finding new situations for their characters, but Hacks found five seasons of new ways for its central relationship to evolve, without ever losing the friction that made putting these two women in the same room so hilarious in the first place.
3
‘Boardwalk Empire’ (2010–2014)
Boardwalk Empire tracks one of the most fascinating periods in American history. The five-season epic begins in Atlantic City at the dawn of Prohibition, with political treasurer Enoch “Nucky” Thompson (Steve Buscemi) realizing almost immediately that banning alcohol is going to make the right people extremely rich. Nucky already controls much of the city through political connections and corruption, but bootlegging gives him a chance to expand far beyond New Jersey. His local operation soon connects him to gangsters, politicians, businessmen, and rival organizations across the country, and the stakes just keep expanding from there. Boardwalk Empire’s historical progression is what gives this story a sense of scale that becomes more impressive with every season.
Nucky initially looks like the man perfectly built for this new America, but it starts feeling like he is in way over his head when his protégé Jimmy Darmody (Michael Pitt) turns against him. Every time Nucky survives yet another rival, the show makes it clear that he cannot keep up with the changing criminal world around him forever. Boardwalk Empire Season 5 makes that shift impossible to ignore with a time jump. The show follows one man building an empire while simultaneously showing how history makes his version of power obsolete. Perfectly capturing a story like that across five seasons is no small feat.
2
‘Six Feet Under’ (2001–2005)
Six Feet Under tells the audience exactly how every story eventually ends, and then spends five seasons proving how everything that came before it is what matters. The drama, created by Alan Ball, follows the Fisher family, who run a funeral home in Los Angeles. After patriarch Nathaniel Fisher Sr. (Richard Jenkins) dies suddenly, his sons Nate (Peter Krause) and David (Michael C. Hall) are left to run the family business alongside their mother Ruth (Frances Conroy) and younger sister Claire (Lauren Ambrose).
Now, one would assume that being surrounded by death every day has prepared the family to deal with it, but it turns out they are just as confused about life as the grieving families who give them business. That contradiction gives the show five seasons of material without requiring increasingly ridiculous stakes. Everyone in the Fisher family is dealing with the loss in their own way, but Nathaniel’s death also forces them to confront whether they are actually living the lives that they want to. By Season 5, the audience is so attached to these characters that the whole emotional ending in the final episode feels strangely beautiful instead of bleak.
1
‘The Wire’ (2002–2008)
The Wire might just be the best show ever created. The series begins with detective Jimmy McNulty (Dominic West) pushing his department to investigate drug kingpin Avon Barksdale (Wood Harris) and his organization, but that first case quickly exposes how much bigger the problem really is. The show turns the city of Baltimore itself into the main character to show how crime is connected to practically every institution around it. McNulty and his team can spend months building a case against Avon, but their work is constantly shaped by higher-ups worried about statistics, appearances, and closing cases more than actually fixing the conditions that create them. Every breakthrough is complicated by police politics, budgets, and unimaginable bureaucracy. At the same time, the show follows Stringer Bell (Idris Elba), who is trying to make the drug trade function more like a legitimate business, while young dealers on the corners are treated as replaceable pieces in a system much larger than them.
Now, The Wire refuses to keep its critique of the system confined to narcotics. Season 2 shifts the focus to the city’s dying docks; Season 3 brings the focus back to the streets as City Hall begins shaping what the police are allowed to do; Season 4 covers the public schooling system, while Season 5 turns toward journalism. The interesting part is how all of these institutions are interconnected, even when the people inside them rarely see the full picture. That is also why characters who seem powerful in one part of the city can look completely powerless in another. More than two decades later, The Wire still feels like a timeless piece of television that somehow keeps becoming relevant all over again. If there is one HBO classic every serious television fan should experience at least once, this is it.
The Wire
- Release Date
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2002 – 2008-00-00
- Network
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HBO
- Directors
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Ernest R. Dickerson, Ed Bianchi, Steve Shill, Clark Johnson, Daniel Attias, Agnieszka Holland, Tim Van Patten, Alex Zakrzewski, Anthony Hemingway, Brad Anderson, Clement Virgo, Elodie Keene, Peter Medak, Rob Bailey, Seith Mann, Christine Moore, David Platt, Dominic West, Gloria Muzio, Jim McKay, Leslie Libman, Milcho Manchevski, Robert F. Colesberry, Thomas J. Wright