Timothy Olyphant has made a career playing famous lawman roles, though some are better than others. Olyphant began his rise to stardom in the late 90s with standout roles in Scream 2 and Go, before landing his big break on Deadwood, the acclaimed Western HBO series. Over the years, Olyphant has become a Western TV icon for modern audiences with a number of roles in the genre or playing on his image in the genre.
Olyphant’s career is filled with more versatile roles, from comedies to thrillers. He will even appear in the upcoming Alien: Earth as the latest android in the Alien universe. However, it is hard to deny that Olyphant finds a lot of success in playing various lawmen. From detectives to marshals to government agents, Olyphant has amassed a number of these characters. Some are noble officers, others are corrupt, and others fall somewhere in the middle.
8
Snowden (2016)
As CIA Agent Geneva
Snowden is based on the true story of Edward Snowden, a former CIA contractor who turned whistleblower, publicizing classified documents to the public. Joseph Gordon-Levitt stars as Snowden in this Oliver Stone movie that explores his life and the revelations within the government that led him to expose these secrets. Timothy Olyphant appears in a smaller supporting role in the movie as Snowden’s CIA superior in Geneva, whose shady tactics in getting a key asset to cooperate lead Snowden to resign.
There’s not a lot to the character beyond showing the darker aspects of these government jobs.
Olyphant’s role is not a big one, but he pulls off the slick operator part effortlessly. This CIA field officer is confident and effective in his shadowy work, but there is a villainous underlying tone to the performance, with his remorselessness about the morally grey areas of the job. There’s not a lot to the character beyond showing the darker aspects of these government jobs, and it would have been interesting to see it fleshed out a little more, but Olyphant does fine with what he is given.
7
Gone In 60 Seconds (2000)
As Detective Drycoff
Timothy Olyphant was still an up-and-coming actor when he joined the star-studded cast of Gone in 60 Seconds. The movie stars Nicolas Cage as Memphis Raines, a reformed criminal who has to return to his car theft days in order to pull off an impossible job to save his brother’s life. Olyphant appears as Detective Drycoff, the younger partner of Detective Castlebeck (Delroy Lindo), who is hunting Raines.
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Olyphant doesn’t get a lot to do in the role, but his effortless charm and swagger do allow him to stand out in what could have been a pointless role. He also shares some solid chemistry with Lindo. However, Drycoff is ultimately too small a cop character to really compare to most of Olyphant’s other lawman roles. Without any real defining moments, he is just another member of the ensemble and nothing more.
6
Havoc (2025)
As Vincent
The most recent of Timothy Olyphant’s cop roles sees him playing the rare villainous lawman. Havoc comes from director Gareth Evans (The Raid) and stars Tom Hardy as a flawed and morally gray detective who is tasked with saving the son of a politician from the city’s criminal underbelly following a drug deal gone wrong. Olyphant plays Vincent, Hardy’s former partner, who leads a team of crooked cops looking to get their hands on the drugs.
The movie’s story is certainly messy and can take away from some of the thrills, but it is an action-packed ride with some wild sequences. Olyphant gets in on the action as a detestable villain, but he also brings his signature charm to the movie, which makes it fun whenever he appears in the story. He handles the ruthlessness of the character nicely, without being over-the-top. However, with so many other villains and conflicts, he doesn’t get as much screen time as he should.
5
The Mandalorian (2020)
As Cobb Vanth
It was a surprise to see Timothy Olyphant step into the Star Wars universe, but also a treat to see that he was bringing a lot of aspects of his most famous roles. Olyphant appeared as Cobb Vanth for the first time in the season 2 episode of The Mandalorian, “The Marshal”. Vanth is a character taken from the extended Star Wars universe, a sheriff on Tatooine who acquires the Mandalorian armor previously worn by Boba Fett.
While fans only got a few episodes with Vanth, seeing Olyphant brings his Western hero persona to the Star Wars universe is a thrill.
Vanth makes a return in the Star Wars universe in season 1 of The Book of Boba Fett, where he faces off in a showdown with fan-favorite Star Wars anti-hero Cad Bane. While he is thought to have died in that duel, the post-credits scene for the first season of The Book of Boba Fett teases that Vanth may return in the Star Wars universe.
While fans only got a few episodes with Vanth, seeing Olyphant brings his Western hero persona to the Star Wars universe is a thrill. Hopefully, he’ll get the chance to flourish more in the role with some more appearances in the near future.
4
Fargo (2020)
As Dick “Deafy” Wickware
The crime anthology series Fargo brings in a new cast of colorful characters each season, with some big names joining the show. Season 4 of Fargo saw the likes of Chris Rock, Jessie Buckley, Jason Schwartzman, and Ben Whishaw for a story of two crime families in 1950s Kansas City. Olyphant has a supporting role in the season as the Mormon US Marshal Dick “Deafy” Wickware searching for two escaped convicts.
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While Olyphant as a US Marshal might bring some other roles to mind, Deafy is a very different lawman than some of those other characters. He is a religious man who doesn’t abide by swearing or taking the Lord’s name in vain. However, he is also a cruel bigot who brags about viciously murdering Italians. Unlike some of the more iconic lawman roles from Olyphant, Deafy is more of a supporting player in the story, only appearing in seven episodes of the season.
However, Olyphant steals every scene he is in as the complicated Marshal. He dives into the rich dialogue, delivering a captivating performance even if it is not front-and-center. He is especially good in a head-to-head scene with Rock.
3
The Crazies (2010)
As Sheriff David Dutton
The Crazies is sadly one of the lesser-known projects in which Timothy Olyphant played a lawman role, but it remains one of the best. A remake of a George A. Romero horror movie, The Crazies stars Olyphant as David Dutton, the sheriff of a small community where a virus begins spreading through the population, turning the infected into emotionless, violent killers. As the military takes drastic measures to ensure the virus doesn’t spread, David desperately tries to get his wife and friends out of town and to safety.
Despite the horror setting, Olyphant’s David is a grounded hero who is vulnerable in a situation that is over his head. He is a capable man, but he is also scared for his loved ones. Olyphant brings a lot of emotion to the role, including one standout moment in which David lovingly tells his wife that if she wants to give up, they can meet their fates together. It is a performance that elevated The Crazies and makes it an underrated horror gem.
2
Deadwood (2004-2006)
As Seth Bullock
Deadwood is drawn from real history and finds Timothy Olyphant playing the only real-life lawman thus far in his career. It is also the only traditional Western from Olyphant, taking place in the lawless town of Deadwood as it focuses on a collection of characters, both good and bad, who are trying to find their fortune in the town. Olyphant plays Seth Bullock, a former sheriff who comes to Deadwood looking to become a business owner. However, his noble principles and short temper led him to return to his lawman role.
Olyphant returned in Deadwood: The Movie, with Bullock now a marshal and no less aggressive when taking on injustice.
While Ian McShane’s Al Swearengen steals the show as the foul-mouthed gangster, Olyphant gives a subtle and excellent performance as Bullock. He is a man who is always concerned with honor and respect, but whose temper can also lead him to act recklessly. The moments of him facing off with Al are among the highlights in the show and make it even more entertaining when they form an unsteady alliance in later seasons. Olyphant returned in Deadwood: The Movie, with Bullock now a marshal and no less aggressive when taking on injustice.
1
Justified (2010-2015)
As Raylan Givens
Even with such a versatile career, the role of Raylan Givens in Justified stands out as the most iconic Olyphant has taken on. Raylan is a US Marshal who is sent back to his hometown of Kentucky after shooting a gangster in broad daylight. Back in his old community, Raylan reignites old flames, revisits old rivalries, and contends with the local criminal element, including his old friend, Boyd Crowder (Walton Goggins).
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Olyphant received an Emmy nomination for his performance, with Raylan being the perfect character to showcase the actor’s various talents. He is a slick hero who proves himself the fastest gun out there many times over. He is also a hot-headed and arrogant lawman who is not afraid to bend the law to suit what he thinks is best. The role also shows Olyphant’s gift for comedy with Raylan’s hilarious one-liners, putting the criminals down.
Justified is a brilliant neo-Western with Raylan feeling like a cowboy who stepped right out of the Old West. Even with all of his flaws, it is a thrill watching him bring that old-fashioned sense of justice to a modern setting. Olyphant reprised his role in the limited series Justified: City Primeval, proving he still had all the swagger that worked so well the first time.