Timothy Olyphant’s 7 Greatest Thrillers, Ranked: Villains, Action and Dark Comedy

A career beyond Westerns

Olyphant became widely recognized through television Westerns such as Deadwood and Justified, while also building a film career. He was once considered a possible leading man, but the right movie to make him a major star never arrived.

He has continued to appear on television, including in Alien: Earth and Lucky, and returned to film with Over Your Dead Body. He is also set to play actor James Stacy in The Mis-Adventures of Cliff Booth, a Netflix follow-up to Once Upon a Time in Hollywood.

Villainy in A Man Apart

In the early-2000s thriller A Man Apart, Vin Diesel plays a police officer grieving his wife’s murder. The revenge story feels familiar, though director F. Gary Gray’s action work and the supporting cast help sustain it.

Olyphant plays Hollywood Jack, a villain whose humor cuts through the film’s grim tone. His character’s killing of an associate stands out as the movie’s most shocking moment, and the performance makes a strong case for giving Jack a larger role.

Havoc and Die Hard

Gareth Evans’ Netflix film Havoc pairs Tom Hardy with Olyphant in a crime story whose action sequences are stronger than its thriller elements. The movie shifts among a corrupt detective’s moral struggle, stylized action and a 1970s-inspired police story without settling on one approach.

Hardy, Olyphant, Forest Whitaker and Luis Guzmán give the film an engaging cast. In Live Free or Die Hard, by contrast, Olyphant’s hacker villain is viewed as a weaker part of the film, lacking the spark associated with earlier franchise antagonists.

The fourth Die Hard film drew criticism for its PG-13 rating, which reduced the violence and language of previous installments. Its unrated cut restored those elements, while Bruce Willis and Justin Long provide a likable pairing despite the film’s implausible action and near-invincible version of John McClane.

A dark comic turn

Over Your Dead Body remakes the Norwegian thriller The Trip, combining dark comedy with horror elements. Jason Segel and Samara Weaving play spouses whose plot to kill each other is interrupted by a criminal gang.

The increasingly grim events leave no clear hero, but the film’s gruesome content does not make it an unpleasant watch. Segel and Weaving lead the story, while Olyphant supplies a welcome comic presence.