Elliott played against his non-threatening and almost sweet average guy looks, going on to frequently portray characters ranging from the oddly creepy to all-out maniacal in turns that defined "obnoxious". Elliott appearance on screen was always greeted with hearty laughter by his numerous fans, a disconcerting fact for directors like Michael Mann and James Cameron who had more serious aims. The actor made his feature debut in Mann's psychological thriller "Manhunter" (1986) and his first TV dramatic guest spot on CBS' "The Equalizer" in 1987. He went on to pen and star in two Cinemax comedy specials in 1987, and appeared in the Francis Ford Coppola-directed segment of "New York Stories" and Cameron's undersea thriller "The Abyss" (1989). Elliott gained a small but devoted following as the creator, producer, writer and star of "Get a Life!" (Fox, 1990-92), a defiantly stupid but groundbreaking and often wildly funny sitcom about a 30-year-old paper boy.
Elliott's feature career resumed with substantial supporting roles in two 1993 features: the hip-hop spoof "CB4" and the superior Bill Murray vehicle, "Groundhog Day". He became a feature lead (and provided the story) with "Cabin Boy" (1994), an amiably stupid and pleasingly stylized comedy co-produced by Tim Burton and featuring a David Letterman cameo. While certainly not an Oscar contender, "Cabin Boy" was excessively ravaged by critics and earned punchline status along the lines of the far worse "Ishtar", although Elliott's project was far more humble and amusing. Still, the film achieved cult status and was celebrated among his large and loyal fan base.
Elliott followed up this disappointment with an equally lackluster stint on "Saturday Night Live". As a member of cast in the wayward 1994-1995 season (which featured Janeane Garofalo and marked the exits of Adam Sandler, Chris Farley and David Spade), Elliott was given few onscreen opportunities and got even fewer laughs in this format that just didn't foster his unique comedy. He fared better with series guest work, including stints on the sitcoms "Murphy Brown" (CBS), "The Simpsons" (Fox), "Wings" (NBC) and "Sabrina, the Teenage Witch" (ABC). In 1997 he joined the cast of the troubled sitcom "The Naked Truth" (NBC) as an eccentric photographer for a sleazy tabloid and failed to make much of a mark on this series which, by his own accounts, was a rather unpleasant experience.
Elliott returned to form with a supporting role in the Farrelly brothers comedy hit "There's Something About Mary" (1998), playing Ben Stiller's terribly creepy friend Dom, a man with a nervous skin condition that renders him rashed around the Cameron Diaz-portrayed titular dream girl. Television beckoned again, and Elliott lent his voice to power-crazed Dogbert on UPN's animated series "Dilbert" (1999-2000). Before embarking on his next role as the doctor pal of Steven Weber in the off-beat NBC fall sitcom "The Weber Show/Cursed" (2000-01), Elliott took a co-starring role as a lunatic snow plow operator in the family comedy "Snow Day" (2000), then appeared as a restaurant manager in the hit Eddie Murphy comedy "The Klumps" (2001) and had a key role in the comedy sequel "Scary Movie 2" (2001) before reuniting with the Farrellys for the part-animated "Osmosis Jones" (2001).
Taking a break from film, Elliott became a regular guest star on several popular series, including "The King of Queens," "Ed," King of the Hill," "Still Standing" and in a recurring role as Reverend Gaylord Pierson on "According to Jim." But Elliott may be best remembered for his recurring stint as Robert Barone's oddball comic book-loving brother Peter McDougal on the hit sitcom "Everybody Loves Raymond" beginning in 2003 and lasting through to the series finale in 2005.
In addition to a full television and film acting career, Elliott gained exposure with memorable work as the unlikely pitchman for Tostitos in the late 1990s.