Timothy Olyphant has been working in Hollywood since 1995. His mischievous smile, witty sense of humor, and physical appearance have made him a staple of movies and TV shows, usually as either a villain or a law enforcer, with no middle in between. Over the years, Hollywood has discovered his playfulness and comedic gifts and has started using him in roles where he can use those qualities. Olyphant has had many great performances, including: A Perfect Getaway, The Broken Hearts Club, The Girl Next Door, and Once Upon a Time in Hollywood. What are Timothy Olyphant’s best performances, then? Glad you asked:

MOVIEWEB VIDEO OF THE DAY

8 The Mandalorian (2020-Present)

     Disney

When you need a sheriff, who are you going to call other than Olyphant? That’s what Favreau might’ve thought, as he used him in The Mandalorian. Olyphant plays Cobb Vanth, the Marshal of Mos Pelgo, and as always, his charisma and cockiness make him the coolest lawman ever. He might fire a blaster and not a gun, but Olyphant is still a hero here, willing to have a duel with whoever thinks they are faster than him, to protect his people. If Star Wars needs another TV show, The Marshal, played by Olyphant, could be a great idea.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

7 Scream 2 (1997)

     Konrad Pictures

Scream 2 showed that the franchise had legs and could still be both scary and meta all at once. It might not be the best Scream movie, but it has elements that make it the most important sequel of all. Regarding Olyphant, this is the role where many people first met the actor. When the role calls for it, he has always known how to up the menacing acting and the crazy look, and those qualities were essential for playing Mickey. He might look like a film geek obsessed with sequels, but in the end, he shows his true colors, as he’s the new Ghostface. He’s intense from the start, but once his true intentions are revealed, he stops being a quirky guy and becomes extremely creepy. It was Olyphant’s first big role, and it’s still remembered.

6 Live Free or Die Hard (2007)

     Cheyenne Enterprises

In Live Free or Die Hard Olyphant is again the villain, playing the cyber-terrorist Thomas Gabriel. John McClane (Bruce Willis) is the only one that can frustrate his plans to show the government how easy it would be to put the country in trouble. Olyphant plays smart, sleazy, cruel, and frustrated in this film, and has a blast with every moment. He might not get to Alan Rickman’s level of villainy (nobody can), but he shows how strong his “ends justify the means” philosophy is. His character believes he’s the hero of the story, and we understand how he feels, all the way to the end, in a pretty surprising death.

5 Rango (2011)

     Paramount Pictures 

Rango is an incredible western-inspired animated movie, about an ordinary chameleon who ends up being the sheriff in a town run by outlaws. Although being an animation film, this might be Gore Verbinski’s best film ever. Olyphant plays the “Spirit of the West”, a mysterious character who shares many similarities with Clint Eastwood. It might look like a simple voice cameo, but Olyphant imbues the character with all the weight of Eastwood’s voice, making an impression in his short role that’s essential for Rango’s journey. It wasn’t Olyphant’s first cowboy, and it wouldn’t be his last.

4 Santa Clarita Diet (2017-2019)

     Kapital Entertainment

Santa Clarita Diet tells the story of Sheila (Drew Barrymore) and Joel (Olyphant) Hammond, a married couple who work as real estate agents in Santa Clarita. Their lives change when Sheila starts to become a zombie. This series lets Olyphant loosen up and finally show off the comedic chops he had used in many late-night TV show appearances. He plays the exasperated husband, who tries to normalize her wife’s condition in one of the best zombie TV series ever. He’s hilarious, always game, and knows how to show real love and affection for his family. It’s a good change of pace for Olyphant, after many lawmen and villains, and showed how good he could be in a comedy.

3 Go (1999)

     Touchstone Pictures

Go is a movie that’s been sadly forgotten. It has a lot of energy and an incredible young cast (Katie Holmes, Sarah Polley, Taye Diggs, Scott Wolf, Jay Mohr, and Olyphant) in a movie that has many genres. At times, it is a comedy, a thriller, an action movie, a drug-induced party, and much more. Olyphant plays Todd Gaynes, the drug dealer with a Santa hat. He’s menacing, charismatic, dangerous, and slimy all at once in a performance that jumped off the screen. The director, Doug Liman, told The Ringer he considers Go his best film: “We’re so trained toward short-term rewards that the true success of a movie has to be evaluated in 10 or 20 years after it comes out, and so, if you ask how I feel about how [Go] was received from where I sit today, I couldn’t be more proud of it, and it couldn’t have been received better,”

2 Deadwood (2004-2016, 2019)

     Roscoe Productions

Deadwood was an incredible and unique show, written by the genius, David Milch, that told the story of the real-life town of Deadwood, South Dakota. Olyphant played the sheriff, Seth Bullock, in one of the most central roles in the show, infusing his character with honor, bravery, and morals in a town with none of those traits. Not all actors could recite David Milch’s Shakespearean dialogue and work with his improvising methodology, but Olyphant thrived in those circumstances, creating a still-talked-about character, and one that only Milch could write. Kim Dickens told Yahoo about the writer: “On the other hand, David is there with just this poetry flowing out of him, of insight and knowledge, and inspiration.”

1 Justified (2010-2015)

     Rooney McP Productions

Justified was a TV show based on one of Elmore Leonard’s characters: Marshal Raylan Givens. It was the role that Olyphant was born to play. He’s a lawman, but tweaks the rules when it suits him, looking for the best outcome for the common people, even if that means shooting first. Olyphant gave an incredible performance as Givens. He was cocky, fun, charismatic, smart, and dangerous in what was one of Elmore Leonard’s best film and TV adaptations. We’re lucky, as Justified is coming back, so we haven’t seen the end of Raylan Givens. We can’t wait for Olyphant to put on the hat again and show us new layers in his best performance, ever.