Raised in Ottawa, Green began to hone his comic skills as a teenager, pulling gags for the amusement of his friends. Along with doing stand-up while in college, Green released a rap album and created a hit radio show at the University of Ottawa. After graduation, Green managed to get the first incarnation of his signature TV series, The Tom Green Show, on local Ottawa television in 1994. A hit, The Tom Green Show landed on Canada's Comedy Network and officially hit the big time when MTV bought it and began airing it in the U.S. in 1999. During its two years on MTV, the show garnered high ratings due to Green's penchant for pushing the limits of taste with such gags as shagging a dead moose and delivering animal parts to his parents' house, and for involving innocent bystanders in his "confrontational comedy." Green even managed to top the episode featuring his trip home with Presidential paramour Monica Lewinsky when he transformed his spring 2000 battle with testicular cancer into the infamous "Cancer Special" for MTV.
During Green's MTV tenure, he moved to films with a small role in the Saturday Night Live-based comedy Superstar (1999). Green's antics as a nerdy college student, particularly placing a live mouse on his tongue, subsequently became one of the main draws of the raunchy teen hit Road Trip (2000). A cameo as Drew Barrymore's sad sack boyfriend Chad in the blockbuster Charlie's Angels (2000) paid off personally when Green and Barrymore became an offscreen item; after much hedging and a faux jilting at the altar on Saturday Night Live in November 2000, the two married quietly in 2001.
After The Tom Green Show ended, Green turned his attention to his first movie vehicle, co-writing, directing, and starring in Freddy Got Fingered. Avowedly intended to be the most disgusting film possible, Freddy featured such set pieces as Green swinging a baby by its umbilical cord, doing unmentionable things with horses, and many creative uses for meat. Although Green's cinematic escapades earned a few comparisons to 1970s performance art, Freddy Got Fingered was mostly blasted for its technical crudity and general witlessness, and died a swift death at the box office.