Having previously appeared in minimal roles in "The First Wives' Club" (1996) and "A Life Less Ordinary" (1997), Olyphant followed up his success with a featured turn as alluring drug dealer Todd Gaines alongside a host of young actors including Katie Holmes, Sarah Polley and Taye Diggs in the ensemble of Doug Liman's "Go" (1999). Although "Go" had a significantly smaller audience than "Scream 2", Olyphant made his mark with a more visible character and his image even appeared on the film's theatrical poster. The actor's strong performance in this challenging and memorable role would help to propel his career further.

Olyphant went on to star as a bisexual actor in the independent feature "Advice From a Caterpillar" (also 1999), featuring Cynthia Nixon, Jon Tenney and Andy Dick. He would then go on to appear in a string of films that, while not necessarily commercial hits, kept his profile up in challenging roles, including the gay-themed ensemble film "The Broken Hearts Club: A Romantic Comedy" (2000); the mystery "Auggie Rose" (2000); the car-theft actioner "Gone In Sixty Seconds" (2000); the comedy "Rock Star" (2001); the suburban drama "The Safety of Objects" (2001); the Vin Diesel crime drama "A MAn Apart" (2003); and as one of the childhood friends menaced by a mysterious force in the Stephen King thriller "Dreamcatcher" (2003).

Olyphant made his television debut in an episode of the short-lived CBS series "Mr. & Mrs. Smith" (1996). The following year, he took a recurring role on the ABC police drama "High Incident" as well as a featured role in the acclaimed CBS TV movie "Ellen Foster". Olyphant additionally guest starred on HBO's comedy series "Sex and the City" as a younger man romancing Sarah Jessica Parker and offered a supporting turn in the network's World War II-set original movie "When Trumpets Fade", starring Frank Whaley and Ron Eldard (both 1998).

In 2004 Olyphant achieved a fresh bout of exposure when he was tapped to star in "NYPD Blue" creator David Milch's much-anticipated Western drama series "Deadwood" for HBO, playing Seth Bullock, a man looking for a new start in the lawless frontier town. He also enjoyed a scene-stealing supporting role on the big screen as a porn producer looking to lure his top actress (Elisha Cuthbert) back into the business in "The Girl Next Door."