Rolston played PFC M. Drake in Aliens, Hans in Lethal Weapon 2, Stef in RoboCop 2, Bogs Diamond in The Shawshank Redemption, J. Scar in Eraser, Chief Dennis Wilson in Daylight, Wayne Bryce in Hard Rain, and Special Agent in Charge Warren Russ in Rush Hour. Rolston also acted in Martin Scorsese's film The Departed and the television horror film Backwoods. Many of Rolston's screen roles are villains due to his trademark icy stare. He also co-starred in Saw V, and Saw VI.
In 1994, he portrayed convicted killer "Karl Mueller" in the Babylon 5 episode "The Quality of Mercy," as well as "Richard Odin," leader of a vegetarian cult in an episode of the X-Files called "Red Museum." He was also originally considered to voice the supervillain Firefly in Batman: The Animated Series, though the character was deemed unsuitable for the series and ultimately dropped. Rolston would later voice Firefly in the revamp, The New Batman Adventures, as well as Justice League. In 2004 Rolston would guest star in two episodes of the critically acclaimed 24.
He also appeared in a minor role in The CW series Supernatural in season 4 as the demon Alastair.
He had a voice-acting role in the video games Blade Runner, and Turok, as well as Halo 4. He also appeared in Criminal Minds in the episode, "Blood Hungry" as Sheriff Don Hall who asks for the BAU's help in finding out who's behind a series of violent murders.
He voiced Deathstroke in Batman: Arkham Origins, where he replaced Ron Perlman who was absent while working on the upcoming Fallout 4.
He has a recurring role as Lex Luthor in the animated series Young Justice.