As with the rest of the Spin City main cast, Chaplin has featured in creator Bill Lawrence's subsequent sitcom, Scrubs, playing a drug addict who tries to trick Elliot into giving him prescription medication in "My Moment of Un-Truth" and later tricks Jordan into giving him money in "My Rite of Passage". His character later appeared in "My Scrubs" as a drugs counsellor for the hospital, claiming to be reformed.
Chaplin also appeared in an episode of Law & Order (Season 14, episode 1, "Bodies") as pompous yet ethical legal-aid attorney Timothy Schwimmer who has to defend a serial killer (played by Ritchie Coaster). Chaplin's character ends up on the stand for not disclosing information, protected by the attorney-client privilege, given to him by the serial killer.
As a teen, Chaplin attended Stagedoor Manor Performing Arts Training Center in upstate New York.