Deadwood is a no-brainer when it comes to naming the greatest shows in television history. The early 2000s HBO drama began as a show focusing on Rome, with creator David Milch pitching to HBO with aims to explore the ways civilization organizes itself and emerges from chaos. However, HBO already had the John Milius series, Rome, and proposed Milch telling his story in another setting and time. The result is a western filled to the brim with memorable characters, honed dialogue, and more profanities in one episode than your average Quentin Tarantino movie. It only lasted for three seasons before being canceled abruptly, only to return over a decade later for a film to wrap things up.
Milch crafted a rich world that was every bit as raw and nasty as the language used by its characters. While it took a while for it to have a fitting conclusion, the influence of the show is undeniable when you see the memorable characters that would follow elsewhere. Sons of Anarchy, Justified, Lost, The Walking Dead, and even The Mandalorian need to tip their hats to Deadwood. The actors who made their mark on the HBO series would filter out into these other projects and performances in the years to follow. Does Timothy Olyphant become Raylan Givens if not for Deadwood?
These characters brought to life for the HBO western are the main attraction, with any list — including the one you’re currently perusing — spoiled for choice when filling the spots. Talents If anything, working through it has brought back a lot of great memories of the series. It’s a reminder that Deadwood is right up there with stuff like The Sopranos, The Wire, and Breaking Bad as some of the greatest TV in history.
Scroll down to see the characters we think cement this idea.
1) Al Swearengen – Ian McShane
Owner of The Gem Saloon and a man who is always hatching a scheme to corner power in the frontier town, Al Swearengen is an anti-hero worthy of the name. McShane commands almost every scene he’s in, with Milch’s dialogue paving the road for him to flex those acting chops. Even when he can’t speak and is passing a kidney stone, he’s still giving orders and owning the screen. These aren’t ranked, but if they were, he’d still be placed at the top spot.
2) Seth Bullock – Timothy Olyphant
Truly one of the most honorable men in the entire series, his relationship with Alma Garret aside, Sheriff Bullock is the light side of Deadwood to Al Swearengen’s dark, cutthroat nature. It’s always hard to fictionalize a notable real-world figure, but Olyphant goes above and beyond. You see a lot of him in Olyphant’s later Justified role, though he gets to play around with a little more charm than Bullock. Still, this is a performance worthy of the sheriff whose grave sits near Calamity Jane and Wild Bill Hickok.
3) Joanie Stubbs – Kim Dickens
The former madam at Cy Tolliver’s Bella Union and later the owner of the Chez Amis, Stubbs is a breakthrough role for Kim Dickens and one of the strongest representations of females on the series. Her relationship with Calamity Jane helps drive her story forward near the end of the series, and continues into the movie despite the decade away. Dickens would go on to appear in Lost, Sons of Anarchy, Treme, and would star in Fear the Walking Dead, but Deadwood is where it all takes shape.
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4) Doc Cochran – Brad Douriff
While he’s best known for lending his voice to the murderous doll Chucky from the Child’s Play franchise, Douriff has never been a slouch when it comes to acting. He was nominated for an Oscar for his role in One Flew Over the Cuckoo’s Nest and later earned an Emmy nomination for his Deadwood role. Amos “Doc” Cochran was a mixture of several real people, but he showcased the dedication and stubbornness required for a doctor’s survival in a town full of miscreants and tyrants.
5) Mr. Wu – Keone Young
For a character who can only communicate with three words in English, his role in the show is memorable, and he’s part of some of the best moments opposite Swearengen and his crew. Truly a real “heng dai.” His dialogue issues also has some layer if you consider how Keone Young is well known as a voice actor, with a major role being Storm Shadow on G.I. Joe. He was also one of the many Deadwood alums to go on to appear on Sons of Anarchy.
6) Dan Dority – W. Earl Brown
Swearengen’s right-hand man, Dority manages to be both imposing and sensitive all at once thanks to the work of W. Earl Brown. He’s a fixture in every episode, delivers one of the most vicious television fights in history, and he’s serious about not putting any cinnamon on the meeting table. He’s just easy to like, even if he’s a bad guy on paper.
7) Cy Tolliver – Powers Boothe
Really, all we need to write here is that Cy Tolliver is played by the late, great Powers Boothe. He’s worth the price of admission. Boothe brings the sinister quality he manifested in countless other projects to his Deadwood role, manifesting a perfect adversary for Al Swearengen and the rest of the town. His loyalties always seem to be for sale, and Boothe plays that type of fella perfectly.
8) Charlie Utter – Dayton Callie
A real-life figure of the “wild west,” Utter was a close friend of Wild Bill Hickok and Calamity Jane, settling in Deadwood with them at the start of the series. After Hickok is slain, he remains in Deadwood, becoming a deputy and an ally to the orderly patrons of the town. He is killed in the Deadwood movie,
9) Calamity Jane – Robin Weigert
Weigert’s portrayal of Calamity Jane Canary is a leathery, boozy, profane, sensitive take on the real-life frontier legend. By far, she’s one of the most interesting portrayals in the series and manages to surprise you in the same ways she’s surprising the other Deadwood residents. Robin Weigert’s performance gives depth to a historical figure in ways we don’t normally get to see.
10) Wild Bill Hickok – Keith Carradine
The legendary gunfighter and gambler comes to Deadwood with Charlie Utter and Calamity Jane, instantly grabbing the focus of the town’s denizens and becoming friends with Bullock and others. Swearengen wants him dead, but isn’t above taking his bribe to put it to good use. His famous death is a big part of season one, and reverberates in the show with Utter and Jane’s reverence, mixed with Bullock maintaining his duties and promises made to his late friend. Also Keith Carradine is just that damn good.
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