Cobb Vanth & 9 Other Iconic Timothy Olyphant Roles, Ranked

Despite acting in many films and shows over the years, Timothy Olyphant has become famous for stealing the show. Rather than being the leading man the likes of Tom Cruise, Will Smith, or Chris Evans, Olyphant has mostly been known for his side character roles and a few TV leading roles.

Now, with the actor appearing in the Star Wars universe as Cobb Vanth and Justified getting the revival it deserves, it is the perfect time to showcase the actor’s many show-stealing roles. Whether he is the star of a TV series or a brief cameo, Timothy Olyphant always delivers on a charming performance.

Cobb Vanth – The Star Wars Universe (2020 – 2022)

Making his surprise debut in the second season of The Mandalorian, Timothy Olyphant portrays Cobb Vanth. Cobb is the Marshal of Mos Pelgo and is one of many examples of Star Wars going full Western. Timothy Olyphant is no stranger to playing cowboys and sheriffs so this role suited him perfectly.

Where most Olyphant characters feature a dark side, Cobb Vanth is a hero of his town. Olyphant plays him as a calm and collected gunslinger but the truth is that he’s a simple man trying to protect his people. Fans were happy to see him make a return in The Book Of Boba Fett, especially when he got to duel the nefarious Cad Bane.

Dick ‘Deafy’ Wickware – Fargo Season 4 (2020)

In another lawman performance, Timothy Olyphant portrayed Dick Wickware aka Deafy on the fourth season of Fargo. Across seven episodes, Wickware is a U.S. Marshal on the hunt for two criminals and like many Fargo characters in the series, he’s equally as captivating as he is quirky.

From having a roll of carrots wrapped up in his pocket to being a nearly unstoppable force in hunting his targets, Wickware was another memorable addition to Fargo. Olyphant carried the role well with his charm and sharp comedic timing.

James Stacy – Once Upon A Time In Hollywood (2019)

Over the years, Timothy Olyphant has made a career out of minor roles that steal the show. Once Upon A Time In Hollywood showed a very fictionalized history of Hollywood filmmaking, and there are a lot of famous faces played by other famous faces.

Timothy Olyphant briefly plays character actor James Stacy, as he and Leonardo DiCaprio’s Rick Dalton work together on the Western series, Lancer. Olyphant’s performance is a stand-out as he effectively delivers on playing two characters: the actor and the character he is portraying, which is not easy for any actor to pull off.

Mickey – Scream 2 (1997)

Timothy Olyphant shined as one of many possible suspects in Wes Craven’s Scream 2. For the first two-thirds of the movie, Olyphant plays the meta-comedy as effectively as Randy, giving little jabs at Hollywood tropes such as commentary about how sequels can be better than the first.

However, Olyphant’s performance changes as he is revealed to be the new Ghostface: he is obsessed with what happened with the first Ghostface and he wanted to make a perfect sequel to it. Olyphant’s performance is creepy and zany, much like Billy’s, but he makes it his own as one of the many Ghostface killers.

Sheriff David – The Crazies (2010)

Taking on the main hero role in a movie, Timothy Olyphant, once again, plays a lawman but in a more contemporary setting. This time he is the sheriff of a small town where a plague drives infected into becoming crazed murderers in this remake of a forgotten George A. Romero film, The Crazies.

Sheriff David showcases Olyphant’s talents as a leading man that he rarely gets to use. David is not only a likable lead but he’s not some indestructible hero, and he goes through horrific events trying to escape this virus. He gets hurt, worn out, and deals with the human emotions that would come from such a disaster.

Spirit Of The West – Rango (2011)

In a wild cameo in Rango, the desperate hero meets the fabled “Spirit Of The West,” who turns out to be Clint Eastwood. Not only does Olyphant look straight out of classic Westerns such as The Man With No Name trilogy, but the voice is so accurate, most would not be blamed if they thought Clint himself made the cameo.

Timothy Olyphant does a stellar impression of the famous actor. For the few minutes that the Spirit Of The West is featured on screen, Olyphant leaves an impact as one of the most memorable parts of Rango.

Joel Hammond – The Santa Clarita Diet (2017 – 2019)

For three seasons of The Santa Clarita Diet, Timothy Olyphant got to show off his comedic side even more, as his character deals with the fact that his wife is a zombie. Rather than being horrified, most of the time he’s just trying to keep things looking as normal as possible.

As a result, his stress combined with his nice demeanor usually makes for hilarious reactions as his wife Abby continues to make things more difficult. Olyphant’s sharp timing and almost genuine reactions to the wild antics make the show an effective zombie comedy.

Seth Bullock – Deadwood (2004 – 2019)

This is the role that started the typecasting of Olyphant in Western-esque roles. He began as Seth Bullock on HBO’s Deadwood, which lasted three seasons. In 2019, it was revived as a movie with the cast returning, including Timothy Olyphant.

From his naturally gruff voice to his accent, it would seem that Timothy Olyphant was born to play this kind of role, whether it’s a modern-day movie, a period piece, or a sci-fi. Seth Bullock remains a favorite Deadwood character as he went from sheriff to U.S. Marshal.

Thomas Gabriel – Live Free Or Die Hard (2007)

It’s hard to top Alan Rickman’s Hans Gruber, but Olyphant’s Thomas Gabriel is still a worthy addition to the Die Hard franchise. In Live Free Or Die Hard, he is the complete opposite of John McClane: he’s young, calculative, and technologically savvy, which makes him an effective cyber-terrorist. However, that’s what helps his rivalry with McClane stand out.

The more McClane foils his plans and taunts him, the less Thomas Gabriel cares about his terrorism plot and starts focusing more on just killing John McClane, who continues to be a stellar action hero. Olyphant portrays the calm and collected side and the vengeful side of the villain with enough charisma to make him memorable but also one of the more realistic Die Hard villains.

Raylan Givens – Justified (2010 – 2015)

When it comes to Timothy Olyphant’s career, most people will say that they discovered him through Justified. Once again, Timothy Olyphant plays a lawman, only this time he’s a deputy who is not by-the-books and is more akin to an officer seen in the Old West.

Raylan Givens was the lead of Justified for six seasons, giving the same cowboy vibe that Timothy Olyphant has become famous for. Olyphant was able to put more layers into Raylan thanks to his less than clean methods and views on justice, thus making him one of his definitive roles.

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