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The Major Comedy Flop That Ruined Tom Green's Career

Ah, the nineties. For a time period so relatively near us in the rearview mirror, the final decade of the 20th century sure feels like a bygone era. 2000s kids may not believe it, but it wasn't that long ago that teens were acid-washing their jeans and getting their song recommendations from "Now That's What I Call Music!," kids were losing their minds over Tamagotchis and Furbies, women all over the world were asking their hairdressers for the Rachel Greene shag ... and Tom Green was sucking on a cow's udder on national television.

In retrospect, the antics of the Canadian shock comic scan like even more of a relic now than many of the decade's other you-had-to-be-there cultural touchstones; his stunts and pranks were so outrageously gross and disturbing that it seems absurd they would ever be allowed on MTV or any other network. But sure enough, "The Tom Green Show" ran for eight highly successful seasons in Canada and the U.S., and Green became enough of a household name to make a play for movie stardom.

Or so it would have been — if his film career hadn't almost immediately crash-landed. There's a reason today's young comedy fans may not be particularly well-acquainted with Green. The 2001 movie he co-wrote, directed, and starred in was a critical and commercial bomb so notorious that it would have been impossible to walk away from it unscathed.

Freddy Got Fingered was immediately considered one of the worst films ever

Released in 2001 by 20th Century Fox, "Freddy Got Fingered" attempted to retrofit the strangeness and shock value of Tom Green's TV pranks for the realm of studio comedy. Green, in his directorial debut, went about such a task by making the film's "plot" — a cartoonist (played by Green) attempts to get an animated series greenlit while weathering the disapproval and disparagement of his father (Rip Torn) — little more than a throughline on which to hang increasingly surreal, tasteless, and disturbing gross-out set-pieces. The final result prompted critics like Roger Ebert to describe the film as "a vomitorium," and earned Green a whopping four Razzies (via IMDb).

The immediate enshrining of "Freddy Got Fingered" as one of the consensus all-time worst movies (via Rotten Tomatoes), along with its poor box office performance, put a premature end to Green's movie career. But things turned out surprisingly well for him: In addition to beating cancer and bouncing back into a steady TV career over the following years, Green saw the reputation of "Freddy Got Fingered" rise significantly as surrealist horror-comedy became more popular throughout the 2000s and 2010s. Nowadays, the film actually has a large number of devoted fans, who consider it an ahead-of-its-time work of transgressive art, a throwback to the obscene masterpieces of John Waters, and even a scathing parody of the filthiness and immaturity at the heart of most American studio comedies.