Baker landed his biggest role to that point as George Clyde, one of the four Bushwackers at the center of Ang Lee's diffuse drama "Ride With the Devil" (1999). While virtually unrecognizable beneath much facial hair and a Southern accent, the actor managed to transcend the film's problems to offer a complex portrayal of a paradoxical Civil War veteran. While espousing Dixie values, Baker's Clyde was progressive enough to have freed a slave (played by Jeffrey Wright) who saved his life. The actor was next cast as an album cover photographer in the little-seen "Sunset Strip" and was part of the first manned mission to Mars in "Red Planet" (both 2000) before once again competing romantically against Adrien Brody, this time for Hilary Swank, in the period drama "Affair of the Necklace" (2001). While his film career appeared to be on the rise, Baker opted for the steady paycheck that that the small screen can guarantee by accepting the leading role in the CBS 2001 fall drama series "The Guardian.” Here he was cast as Nick Fallin, a hotshot lawyer caught with drugs. As part of his plea bargain, Fallin agrees to community service wherein he serves as a child advocate at Legal Aid Services. Despite the somewhat far-fetched plot, Baker managed to invest the character with sympathy.

He next appeared in “The Ring 2” (2005), the inevitable sequel to the surprise hit, “The Ring,” starring Naomi Watts. Baker played the new boyfriend of a former Seattle reporter (Watts) who fled the city with her son (David Dorfman) for rural Oregon after being hunted by the videotaped spirit of a girl murdered by her mother. In the sequel, both mother and son are haunted by the girl once again, despite seemingly destroying the video tape that—if watched—kills the viewer after seven days. Though eagerly awaited and expected to follow its predecessor down the road to box office success, critics derided the movie as derivative, uninspired and senseless—through no fault of Baker’s, of course. He next appeared in George Romero’s “Land of the Dead” (2005), the fourth installment to the “Night of the Living Dead” series. Baker played a burned-out mercenary who dreams of escaping a fortified city, but instead is coerced into protecting it against a horde of invading zombies. Baker next starred in “Something New” (2005), a romantic comedy in which he played a free-spirited architect who goes on a blind date with a career woman (Sanaa Lathan) only to lose her to her potentially match (Blair Underwood).