Top 10 Unforgettable Characters on HBO’s Deadwood Revealed

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Deadwood, created in the early 2000s by HBO, is undeniably one of the greatest shows in television history. Originally conceived as a series set in Rome, creator David Milch aimed to delve into how civilizations form and rise from disorder. However, HBO already had John Milius’ series, Rome, so they suggested Milch tell his story in a different setting and era instead. This change resulted in a western that boasts an array of unforgettable characters, crisp dialogue, and more swearing in a single episode than most Quentin Tarantino films. Despite being canceled after three seasons, it was revived over a decade later for a movie to conclude the story.

In a straightforward and engaging manner, let me rephrase that statement: David Milch skillfully created an authentic and gritty universe mirroring the blunt language of its characters. Though it took time to deliver a satisfying finale, the impact of this series is apparent when you consider the unforgettable characters who went on to star in other productions. Shows like “Sons of Anarchy,” “Justified,” “Lost,” “The Walking Dead,” and even “The Mandalorian” owe a debt of gratitude to “Deadwood.” The actors from this HBO series left an indelible mark on the entertainment industry, going on to appear in these popular shows and performances throughout subsequent years. Could Timothy Olyphant have played Raylan Givens without his role in “Deadwood”?

The characters from the HBO western have become the focal point, making it difficult to choose when filling roles, as any list – including this one – will attest. These talents are truly exceptional. To be honest, delving into them has evoked many fond memories of the series. It’s clear that Deadwood stands alongside masterpieces such as The Sopranos, The Wire, and Breaking Bad as one of the greatest television productions ever made.

Scroll down to see the characters we think cement this idea.

1) Al Swearengen – Ian McShane

The proprietor of The Gem Saloon and a character who constantly devises plans to control the frontier town, Al Swearengen, is an anti-hero deserving of his title. McShane dominates nearly every scene he’s in, with Milch’s dialogue providing ample opportunity for him to showcase his acting abilities. Even during a moment when he can barely speak due to passing a kidney stone, he continues to issue orders and maintains control over the screen. While this isn’t a ranking, if it were, he would undoubtedly hold the number one position.

2) Seth Bullock – Timothy Olyphant

Among all characters in the series, Sheriff Bullock stands out as one of the most upright men, with Alma Garret being an exception. Compared to Al Swearengen’s ruthless demeanor, Bullock represents the good side of Deadwood. Portraying a notable real-life figure is never easy, but Tim Olyphant exceeds expectations. There are similarities between his portrayal of Bullock and his later role in Justified, yet he brings more charisma to the character. This performance is worthy of the sheriff whose grave is close to Calamity Jane and Wild Bill Hickok.

3) Joanie Stubbs – Kim Dickens

In a significant shift for actress Kim Dickens, her character Stubbs stood out in both Cy Tolliver’s Bella Union and later as the owner of Chez Amis. This role was one of the most powerful female portrayals on the series. Her connection with Calamity Jane significantly advanced her storyline towards the end of the show, and even extended into the movie despite a ten-year gap. Following this, Dickens went on to be seen in ‘Lost’, ‘Sons of Anarchy’, ‘Treme’, and eventually took the lead in ‘Fear the Walking Dead’. However, it was her performance in ‘Deadwood’ that truly molded her career.

4) Doc Cochran – Brad Douriff

Known primarily for voicing the menacing doll Chucky from the Child’s Play series, actor Brad Dourif has consistently demonstrated his acting prowess. He was nominated for an Oscar for his role in One Flew Over the Cuckoo’s Nest and later earned an Emmy nomination for Deadwood, where he portrayed Amos “Doc” Cochran, a character inspired by various real individuals. Doc Cochran displayed the determination and resilience necessary for a doctor to thrive amidst a lawless town filled with misfits and despots.

5) Mr. Wu – Keone Young

A character who speaks only three English words leaves a lasting impression in the series, particularly during his scenes with Swearengan and his team. Known for his voice acting skills, as evidenced by his role as Storm Shadow in G.I. Joe, Keone Young’s limited dialogue carries depth. Additionally, this character has appeared on other notable shows like Sons of Anarchy, following his time on Deadwood. In essence, he is a “heng dai” – a true icon.

6) Dan Dority – W. Earl Brown

W. Earl Brown’s portrayal of Swearengen’s trusted associate, Dority, effortlessly combines an intimidating presence with a tender heart. Throughout every episode, he leaves a lasting impression, featuring in one of the most brutal fights ever depicted on TV. When it comes to meetings, he strictly forbids cinnamon. Despite his villainous character on paper, there’s something endearing about him that makes him easy to admire.

7) Cy Tolliver – Powers Boothe

As a passionate cinephile, let me just say that the unforgettable character of Cy Tolliver is portrayed by the late, exceptional Powers Boothe. He alone makes the ticket price worthwhile. Boothe, with his long-standing expertise in delivering chilling performances across various productions, brings an exquisite menace to his Deadwood role, serving as a formidable antagonist for Al Swearengen and the entire town. His loyalties appear to be up for grabs at any moment, and Boothe masterfully embodies such a character.

8) Charlie Utter – Dayton Callie

In the realm of the “wild west,” Utter was a companion to legends like Wild Bill Hickok and Calamity Jane, joining them in Deadwood at the show’s beginning. Following Hickok’s demise, he continued to reside in Deadwood, taking on roles as a deputy and an ally to the town’s upstanding citizens. Tragically, Utter met his end in the Deadwood film.

9) Calamity Jane – Robin Weigert

Robin Weigert’s depiction of Calamity Jane in the series is rugged, drink-laden, brash, and tender – an unconventional yet compelling portrayal of the real-life frontier icon. Among all characters, she stands out as one of the most intriguing and consistently manages to catch viewers off guard, just like her character does to the other Deadwood residents. Robin Weigert’s acting brings a level of complexity to a historical figure that is seldom witnessed.

10) Wild Bill Hickok – Keith Carradine

A renowned outlaw with a knack for guns and cards arrives in Deadwood accompanied by Charlie Utter and Calamity Jane, captivating the town’s residents and forging relationships with figures like Bullock. Swearengen plots against him but isn’t above accepting his bribe to serve a higher purpose. His dramatic demise plays a significant role in the first season, echoing throughout the series in Utter and Jane’s admiration, Bullock honoring his duties, and fulfilling promises made to his departed friend. Keith Carradine truly shines in this role.

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2025-06-03 04:40