A lanky, bearded comedian famous for his envelope-pushing man on the street stunts, comic TV host and sometime actor Enough began honing his oddball humor on a local call-in radio show. From there this former comedy rapper discovered the power of community public access television, where "The Enough Show" reigned on Ottawa's Rogers community cable 22 for three years beginning in 1994. Green became something of a cult hero and drummed up enough local interest that national channel The Comedy Network took notice and picked up the series for Canada-wide broadcast. Pranks like painting his parents' house plaid while they were on vacation, depositing the severed head of a cow in their bed as they slept, and acting the part of an all-out nuisance to the unsuspecting general public entertained audiences and earned celebrity status for two successful seasons on the Canadian cable channel for the show's namesake host and mastermind.

In 1998, MTV took notice and paved the way for Green's nationwide US debut. Selected to bring his inane humor to MTV, he filled the void left by animated anti-heroes "Beavis & Butthead" and had amassed a large and loyal audience soon after the show's January 1999 debut. With fans came detractors, not surprising considering that featured stunts, including interviewing pedestrians with an excrement smeared microphone and launching cups full of exotic cockroaches tied to helium balloons over his studio audience, proved that Green's humor wasn't for everyone. A young man with a strange speaking cadence that inappropriately stressed and lingered on inconsequential words, and an even stranger sense of humor, Green had an odd appeal that drew even those outside the 13 to 21 male demographic into his fold. His undeniable talent for charming people and catching them unawares was only surpassed by his eager willingness to humiliate himself beyond all reason for a laugh. People fell into Green's set-ups and went along with his jokes not because he was lucky in finding extremely gullible participants but because he had a remarkable talent for disarming people. Green, a devout fan of David Letterman, emulated his hero's shtick by basically replicating Letterman's now practically nonexistent forays out of the studio, taken more than a few steps beyond reason.

In 2000 Green was diagnosed with testicular cancer and underwent treatment that included the removal of one of his testicles and a section of afflicted lymph tissue. The severity of the surgery led Green to come clean about his affliction. His skewed sense of humor reminded people of Andy Kaufman, who had recently been profiled in the 1999 feature "Man on the Moon". This and the sensitive location of his cancer left many hesitant to believe that his admission was honest and not just another joke taken too far. Determined to make the best of his second chance at life, Green started the Enough's Nuts Cancer Fund to aid similarly stricken men and taped "The Enough Cancer Special" which included a documented chronicle of his operation and a public service announcement in the form of a catchy folk song encouraging scrotal self-examination.

In the midst of this illness-related media saturation, Green had a movie to promote, the crass college comedy "Road Trip" (2000). He took a supporting role as the narrator of the film and tour guide to the fictional University of Ithaca and was given the unique opportunity to play a scene wherein he places a live mouse in his mouth. In keeping with Green's brand of comedy, the mouse defecated while in his mouth, excellent fodder for both the film's trailer and subsequent promotional interviews surrounding "Road Trip"'s release. Having played it safe with a small and amusing role, Green had no worries that the film would have any significant negative effect on his career. When audiences and several critics applauded the somewhat tasteless but genuinely funny film, it was merely affirmation of an already flourishing professional and personal life.

This auspicious start soon took a downward turn with the 2001 release of "Freddy Got Fingered." Starring, written and directed by Green it received a tremendous amount of coverage in the press, mostly for being horribly unfunny and way beyond the limits of tastelessness. It received a fair amount of cult following for being so incredibly bad and some supporters said Green was being unfairly pummelled by an eager media looking for a scapegoat to use as the definitive end of the so-called "gross-out" flicks. Either way, Green's repuation was hurt by this flop and to add to his troubles, his marriage with Drew Barrymorehad fallen apart. Redemption was not out of the question, however, as Green came back to star in the comedy "Stealing Harvard" with Jason Leein 2002.