In 1993, Fichtner made a significant mark on stage with a well-reviewed breakthrough performance in "The Fiery Furnace” opposite Julie Harris. It was during this time that Fichtner's film career also began to pan out. His early film appearances included a role in the little seen "Ramona" (1990) and a bit part as a police officer in "Malcolm X" (1992). "Quiz Show" (1994) offered more exposure in a minor role as the game show's stage manager. In 1995, he had was featured in "Virtuosity,” "Strange Days" and as a sleazy banker undone by Robert De Niro in "Heat.” He gave a more significant, although less seen performance in Steven Soderburgh's 1995 feature "The Underneath" as Tommy Dundee, an intimidating and unstable club owner who becomes a rival of Peter Gallagher's Michael Chambers. Fichtner's work as the jealous and powerful Dundee caught the attention of casting director David Rubin who recommended him to Kevin Spacey for "Albino Alligator,” the actor's 1997 directorial debut. While undoubtedly already a familiar presence on screen, due to his prolific and strong performances in small parts, it was this film that proved to be his breakthrough role. Fichtner, riveting as a slurring sociopath who creates a hostage situation in a bar, played up the character's volatility with an intense performance that masterfully stopped short of overacting.

Later that year his well-researched turn as Dr Kent Clark, a blind astronomer in "Contact" was also touted, although a good bit of it ended up on the cutting room floor. While his work in that year's "SwitchBack" was less memorable, 1998's action blockbuster "Armageddon" saw him return with a strong supporting turn as the hard-nosed and disciplined leader of an asteroid destroying mission. Through his own research, Fichtner added a realistic element to his character, making Sharp less combustible than he was initially written. The result was a portrait of an Air Force colonel complete with the steadiness that would be expected from an actual pilot to reach that level. In 1999, Fichtner gave an enjoyable comedic performance in Doug Liman's high-energy ensemble film "Go.” The elder statesman of the cast, he played an undercover narcotics officer with an apparent personal interest in his cohorts (Jay Mohr and Scott Wolf).

Fichtner reached leading man status with a 1999 performance opposite Demi Moore in "Passion of Mind,” playing a New York accountant pursuing a book editor (Moore) in this story of a woman who discovers she has a second life in a parallel universe. Another starring role came that year in "The Settlement,” alongside John C Reilly as men involved in an insurance brokering gamble who meet their match in a woman (Kelly McGillis) who is either a terminally ill cancer patient or a talented con artist. He then battled the storm as a commercial fishermen in the feature drama "The Perfect Storm," which co-starred George Clooney and Mark Walhberg. A year later, Fichtner was cast in two war-based features, "Pearl Harbor" (2001) and "Black Hawk Down." (2002). In 2002, Fichtner starred as a renegade doctor who is forced to bend the rules in a constant quest to treat his patients in television drama "Mds." John Hannah, Jacqueline McKenzie and Robert Joy also co-starred in the ABC drama.

After a supporting role as a dissident leader in the widely-panned futuristic thriller, “Equilibrium” (2002), Fichtner joined a stellar cast that included Don Cheadle, Matt Damon, Ludacris and Sandra Bullock in the moving racial drama, “Crash” (2005). He provided his voice for an episode of the animated “American Dad” (Fox, 2004- ), then played a resentful cop trying to mend his relationship with the owner of a local diner (Ed Harris) in the acclaimed miniseries “Empire Falls” (HBO, 2005). Supporting roles in “The Longest Yard” (2005) and “The Chumscrubber” (2005) led to an appearance in “Nine Lives” (2005), an ensemble drama about the everyday travails of nine women. Fichtner played a man whose ex-wife (Amy Brenneman) starts to fall back in love with him after the death of his second wife. Fichtner then returned to regular series work in the supernatural drama, “Invasion” (ABC, 2005- ), playing a sheriff in a small Florida town devastated by a hurricane that may have a connection to aliens from outer space.

After “Invasion” was cancelled after its first and only season, Fichtner returned to features, costarring in “Ultraviolet” (2006) as the sidekick of a beautiful, but lethal genetically modified human (Milla Jovovich) with near-superhuman powers who becomes a rogue warrior hell bent on protecting her race from being destroyed by the very government that created them. In 2006, Fichtner joined the cast of “Prison Break” (Fox, 2005- ) for season two, playing a dogged, but privately troubled FBI agent who hunts down a group of escaped prisoners that includes two brothers (Wentworth Miller and Dominic Purcell) desperately trying to clear their names while looking for a hidden stash of money. After a convincingly sleazy performance as the best friend of a traveling salesman (Guy Pearce) paranoid about dying in “First Snow” (2007), Fichtner played the adoptive father of a fastidious skating prodigy (Jon Heder) who partners with his arrogant, over-sexed rival (Will Ferrell) for doubles competition after both have been banned from skating solo.