Letterman years (1982–1990)
Elliott was hired as a production assistant on Late Night with David Letterman, and was with the show from its beginning in February 1982. In the middle of 1983, Elliott became a writer on the show and his on-camera appearances became more frequent. Elliott became best friends and writing partners with Matt Wickline, another Letterman crew member who was promoted to the writing staff in 1983. Wickline and Elliott pitched Late Night's first theme show, an Emmy-winning interactive episode called "The Custom-Made Show, leading the program to do a series of ambitious experimental one-off episodes. Along with the rest of the writing staff, he won four Emmys for his work on the show and was nominated for an additional six.
Elliott became known in the mid-1980s for playing an assortment of recurring quirky, oddball characters on Late Night, each of which would usually last for a few weeks to a few months, before being retired amidst much mock-fanfare on the show. Elliott and Wickline co-wrote his early pieces on the show, often about characters who had "Guy" in the name, including The Conspiracy Guy, The Panicky Guy, Terminator parody The Regulator Guy, The Fugitive parody "The Fugitive Guy," and most famously, The Guy Under The Seats, a man who lived under the studio audience seating and would get mad at and threaten Letterman.
In 1987, while still working at Letterman, Elliott starred in two Cinemax Comedy Experiment TV specials called FDR: A One Man Show and Action Family. He co-wrote both specials with Letterman writers Matt Wickline and Sandy Frank. FDR: A One Man Show was a fake play about the life and times of Franklin D. Roosevelt (influenced by Frank Perry's 1984 TV movie J.F.K.: A One-Man Show). Elliott looked and sounded nothing like Roosevelt; he portrayed events from his life that never happened, such as a Japanese bombing of the White House, and his crossing the Potomac in a rowboat. By the end of the show, he had performed Gallagher's shtick of smashing watermelons and other soft fruits on stage.
Following these specials, Elliott and Wickline had a falling out, as Elliott had begun collaborating more with fellow Letterman writer Adam Resnick on his pieces on the show. Elliott and Resnick's character bits found him playing self-involved show business people, both real and fake. These characters include Rip Taylor-esque Las Vegas lounge lizard Skylark, talk show host Chris Elliott Jr. (a la Morton Downey Jr.), and exaggerated surreal impressions of Marlon Brando, Jay Leno, and Marv Albert.
As his career on Late Night blossomed, Elliott auditioned to join the cast of Saturday Night Live when Lorne Michaels returned to the program in 1985. He was offered the job but turned it down to stay at Letterman. He began taking small film roles, often as a supporting actor in films such as Michael Mann's Manhunter and James Cameron's The Abyss. He had a small supporting role in an episode of Miami Vice.
