International funnyman Tom Green first started messing around with music when he was a kid, growing up in Ottawa. With a secondhand drum machine and an Akai sampler, he’d loop 70s funk, R&B, and jazz cuts on his Atari computer, making beats and rapping over them.

Of course, Green was also slowly carving out a name for himself as a comedian, performing stand-up at local clubs like Yuk Yuk’s. But, before the Tom Green Show was picked up by MTV in 1999 and his prankster-absurdist comedy entered the mainstream, Green was in a hip-hop group called Organized Rhyme. Their first and only album, Huh!? Stiffenin’ Against the Wall, produced a cheeky hit called “Check the O.R.” — MuchMusic loyalists might remember the video of the fresh-faced trio running around Toronto’s Jane and Finch neighbourhood in caps and oversized bombers. The song was nominated for Best Rap Recording at the 1993 Juno Awards and even won the MuchVibe award for Best Rap Video in 1992.

Green has celebrated many achievements since then. He became one of the most popular comedians of the 90s, writing and starring in the movie, Freddy Got Fingered, which was originally panned by critics for its gross-out shticks, but has since enjoyed a cult following. Green also had his own late-night talk show, he beat testicular cancer and he’s continued to keep his personal brand alive, touring the world.

Earlier this year, Green released The Tom Green Show: a limited edition and vinyl-only album that recalls the name of the series that made him a household name. It’s his first issue since 92, and combines comedy and cultural commentary with hip-hop, punk, electronic, and samples from his TV shows and stand-up routines.

The track “I Wanna Be Friends With Drake” is a spot-on pastiche of Drake, complete with autotune and synth, where Green half-raps, “I know you said ‘No new friends,’ homie, but that’s exactly who I am.” “Far 2 Young 2 Die,” on the other hand, is no joke —  it’s a post-punk banger that would fit right into Depeche Mode’s catalogue.

The album closes with “The Bum Bum Song (Lonely Swedish),” a novelty tune from the original Tom Green Show. Its inclusion — as in the rest of the album — displays an expertly executed dance between the sincere and the silly designed to make you smile — sort of like Green, himself.