A timeline of the most outrageous moments from Tom Green’s legendary career

Depending on your tastes, Tom Green’s ultra-low-budget shock comedy was either the best or the worst thing on late-’90s TV. His show started on Ottawa community television, was picked up by Comedy Central and eventually landed a home on MTV. It led to a storied career: besides fellating cow udders for entertainment value, he also briefly married Drew Barrymore, appeared on The Celebrity Apprentice and started an internet talk show that reportedly inspired Joe Rogan to launch his podcast empire. Now, he’s moved back to small-town Ontario, has a Prime show about his life in the sticks and is touring Canada with his stand-up show this year and next. Here are the six wildest moments from his legendary career.

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1992: Award-Winning Rapper

Before Tom Green was Tom Green, he was MC Bones, the rapper with three-white-guy troupe Organized Rhyme. In 1992, their first single, “Check the O.R.,” wins the Much Music Video Award for best rap video and is even nominated for a Juno. And all that for a verse where Green rhymes “establishment” with “Polident” (yes, the glue for dentures).

1998: A Statuesque Tribute

In keeping with the barely adolescent vibe of The Tom Green Show, many early skits prank Green’s parents. In one, he pushes them too far by installing two life-sized statues of them in flagrante on their front lawn. Before the episode airs, Tom’s father threatens to sue MTV for $1 million if it includes the footage. Then Oprah Winfrey comes to the rescue, hosting an intervention with the Greens on her Mother’s Day special.

1999: The Slut Mobile

In another prank on Green’s long-suffering parents, he decorates the hood of their car with a massive decal of two women enjoying a bit of cunnilingus and the words “The Slut Mobile.” When Green’s dad attempts to sidestep the embarrassment by taking the bus to work, Green hops in the car and follows him, shouting, “Don’t worry if the neighbours see your slut mobile!”

1999: Moose Doctor

After encountering a dead moose on the side of the road, Green and his crew start the cameras and start riffing. Green waves down passers-by to help him nurse the very deceased animal back to life, saying, “Come hump it with me! It’ll get its heart going again.” Those gyrations earn him a shout-out from ­Eminem, who name-drops Green in “The Real Slim Shady”: Sometimes I wanna get on TV and just let loose / But can’t, but it’s cool for Tom Green to hump a dead moose.

2001: Freddy Got Fingered

Green’s feature film follows a downtrodden cartoonist who gets revenge on his overbearing dad by, among other things, airdropping the family home into Pakistan while his father sleeps and then spraying him with bull semen. It is quickly derided as one of the worst movies ever made and wins five Razzies—which Green accepts gladly, rolling out his own red carpet at the ceremony and playing the harmonica until security drags him off the stage.

2021–present

After 15 years in Hollywood, Green moves home and buys a 100-acre property on White Lake in the Ottawa Valley. Incredibly, it’s great for his career: both his recent I Got a Mule stand-up special and the new Tom Green: Country reality show riff on his life in the sticks. Meanwhile, This Is the Tom Green Documentary revisits all these highlights and more.