Bearing the kind of sharp-eyed, vaguely sinister good looks that often get actors cast as charismatic drug dealers or murder suspects, Timothy Olyphant first impressed film audiences playing none other than the resident charismatic drug dealer of Doug Liman's Go (1999). Born in Hawaii on May 20, 1968, Olyphant grew up in California. After attending the University of California, where he swam competitively, the actor made his professional debut in the Playwrights Horizons' production of The Monogamist, for which he won a Theatre World Award for Outstanding Debut Performance. Olyphant's first film appearance came courtesy of a miniscule role in The First Wives Club (1996); somewhat more substantial work followed in 1997's Scream 2, in which the actor was cast as one of Neve Campbell's friends.
After a turn in When Trumpets Fade (1998), a critically acclaimed made-for-TV WWII drama, and a memorable guest-shot on an episode of Sex and the City, Olyphant gave a scene-stealing performance in Go, managing to stand out in an ensemble cast that included Sarah Polley, Katie Holmes, Taye Diggs, and Scott Wolf. His work caught the notice of more than one industry observer, and by the following year, the actor had a number of projects in the works. Included among them were The Broken Hearts Club, a comedy that cast Olyphant as a gay photographer; Gone in Sixty Seconds, which featured him as a detective on the trail of a car thief (Nicolas Cage); and Auggie Rose, a drama about assumed identity in which Olyphant played the ex-cellmate of a dead con man. In 2001, Olyphant would turn up in the tale of an aspiring singer who gets to live a dream, Rock Star.
Once touted as "the next big thing," Olyphant's stock seemed to drop after attaching himself to a string of duds, most notably the aforementioned Rock Star, Dreamcatcher, and A Man Apart, the latter two both released in 2003. Fortunately, the following year saw things looking up for the actor, with a starring role on the critically acclaimed series from HBO, the Western Deadwood. Over the next several years, Olyphant would appear in films like Live Free or Die Hard and I Am Number Four, in addition to a role on the night time drama Damages, as well as the massively popular series Justified.