In 1998, he was featured as a bartender in the noirish "Johnny Skidmarks", an independent feature aired on HBO in lieu of theatrical release, and had a small role as a police officer in "Lethal Weapon 4". 1999 saw him take the role of Benji in an episode of the NBC hit drama "Providence", while the actor added another small role on the big screen to his resume with a turn as a doctor in the comedy "What Planet Are You From?" (2000). In November of that year, Hoffman made quite an impression in his regular series debut, shocking viewers as the despicable stockbroker Freddie Sacker, an "equal opportunity offender", on "The $treet", a Wall Street-set drama that came to a quick end thanks in part to dialogue fueled by too many mentions of Ivy League MBAs and not enough real character development. Though the show came and went in a flash, Hoffman's performance of the slimy Sacker stayed with many who watched the series.
When the following fall came around, Hoffman and co-star Tom Everett Scott had been picked up for roles in the ABC courtroom drama "Philly", and many TV fans were anxious to see just what kind of characterization Hoffman would bring to his assistant district attorney character. Hoffman's skilled character work continued in a string of film roles, including a turn in actor Adam Goldberg's directorial debut "I Love Your Work" (2003) and an uproarious scene-stealing role as a fast-talking, shallow-minded carjacking victim in the thriller "Cellular" (2004).
The actor enoyed a pair of recurring television roles on "The Practice" and "The Bernie Mac Show," both in 2004, before landing his most amusing role to date as the verbose magician/performance artist Patrick, who becomes one of the pals of the slick ladies' man Jake (John Stamos) on the ABC comedy "Jake In Progress" (2005 - ).