Charles' career still lacked the unqualified box-office smash to put him in the major leagues of young talent, and when neither the staggeringly unfunny "Coldblooded" nor "Pie in the Sky" (both 1995), in which he discovered true love with Anne Heche, advanced his feature career, the actor turned to television. He had scored big in his TV-movie debut, "Murder in Mississippi" (NBC, 1990), playing Andrew Goodman, the civil rights worker killed alongside James Chaney and Mickey Schwermer in the summer of 1964, and had also fared well with his second small screen outing, TNT's fine "Cooperstown" (1993), starring Alan Arkin and Graham Greene. Returning to TV, he acted in three movies that aired on HBO over the next two years, beginning with the comedy-suspense thriller "The Grave", followed quickly by the biopic, "Norma Jean & Marilyn" (both 1996), which presented him as Marilyn Monroe's sympathetic friend Eddie Jordan, and the sci-fi actioner "Crossworlds" (1997), which found him caught between two warring worlds after activating a powerful crystal. Charles made series debut as a regular portraying the witty, verbose and slightly neurotic Dan Rydell, one half of a sports newscast anchor team in ABC's Aaron Sorkin-penned comedy-drama "Sports Night" (1998-2000), where he received critical kudos and a devoted cult following.

In a complete change of venue, he had a supporting role opposite Kermit the Frog and Miss Piggy as a federal agent in the kiddie-oriented "Muppets from Outer Space" (1999), then starred in the Showtime telepic "Our America" (2002), based on a true story about two African-American teens who live on the impoverished South side of Chicago who are selected by an public radio producer (Charles) to do a sound portrait about their life in the ghetto and under his mentorship deliver is an emotional depiction of a slice of life that is both disturbing and remarkable. Next up was a supporting role in "S.W.A.T." (2003), the big-budget adaptation of the 70 TV cop drama, playing special tactics team member T.J. McCabe.

After appearing in the ultra-low-budget romantic comedy, “Seeing Other People” (2004), Charles played a Detroit lawman tracking down the same killers as four vigilante brothers seeking revenge for the murder of their adoptive mother in John Singleton’s “Four Brothers” (2005). Starring Mark Wahlberg, Andre 3000, Tyrese Gibson and Garrett Hedlund as the avenging sons, “Four Brothers” was a straight-forward and often violent revenge thriller that either pleased or disappointed critics for its simplistic narrative. Despite the mixed reviews, “Four Brothers” faired well at the box office, earning over $55 million in its first few weeks of release.