Green began his career as an amateur stand-up comedian at Yuk Yuk's Comedy Club in Ottawa, Ontario. While taking a television production course at Algonquin College, Green released Organized Rhyme: Check the O.R., a rap album under the Island Records label. Two music videos were released with the album, one of which earned the band a Canadian Juno award nomination.

After the release of the album, Green developed and hosted The Midnight Caller, a radio show that aired on the University of Ottawa's station CHUO. The show was the most popular on the station for several years.

After graduating from college, Green pitched an idea for a talk show to Rogers TV in Ottawa. After only four episodes, The Tom Green Show was already a hit with viewers and media alike. Three years later, the show was picked up by The Comedy Network where it has continued to grow in popularity on a national level. Green not only stars in the show, but also wrote, edited and created the music for the series.