Classified attended Hants East Rural High in Milford, Nova Scotia. He started his own production label, Half Life Records, and released his first full length LP called Time's Up, Kid in 1995. After years of working on music and sorting through label contracts, Classified produced, recorded and released his ninth album, Trial & Error, and signed a nationwide distribution deal with Toronto-based, URBNET Records. Containing collaborations with up-and-coming Canadian artists like Eternia and DL Incognito, as well as Canadian rap veteran, Maestro, the album was one of the highest selling independent rap albums in Canada in 2004.
In addition to the release of Trial & Error, 2003 and 2004 were busy and evolutionary years for Classified. With the continuous support of VideoFACT, he was able to release two additional music videos for the singles "Just the Way It Is" and "Unexpected". Classified also continued to master his production skills and joined forces with some of Canada's most prominent emcees, including Choclair and Maestro Fresh Wes. He also teamed up with Shady Records recording artist, Royce Da 5'9" and opened for Ludacris, Snoop dogg, Busta Rhymes, The Game, Nelly, MC Grizzly, Captain Capota, Nas, The Black Eyed Peas and Black Moon.

Classified's tenth album, Boy-Cott-In the Industry, was a high point in his career. The album includes guest appearances by Choclair, Royce Da 5'9", Jay Bizzy, J-Bru, A-Wall, Spesh K, and Mic Boyd (Classified's younger brother and fellow MC). He has said he enjoys doing music with other people: "It keeps things exciting and there are tons of talented people in Halifax so you make connections 'cause it's not a huge scene." The album reached #46 on SoundScan's Canadian R&B/Hip-Hop albums chart. The singles "The Maritimes", "5th Element", "No Mistakes", and "Find Out", which is the lead single of his 11th studio album, Hitch Hikin' Music, were all Top 20 hits on MuchMusic and MTV Canada that year. The music video for "No Mistakes" won him an MMVA for MuchVibe Best Rap Video. Boy-Cott-In the Industry also earned Classified a Juno Award nomination for Rap Recording of the Year in 2006.

Riding high off of Boy-Cott-In the Industry, Classified released his eleventh album Hitch Hikin' Music. Produced like previous albums by Classified himself, it is arguably some of Classified's finest work. On "Fall From Paradise", Classified reflects on the difficulty of staying fresh and on top. In the hip-hop meets classic rock song "All About U", featuring singer Chad Hatcher, Classified shows the extent of his growth from his early releases. In "Hip Hop Star", he eschews the current bling-bling culture of popular hip hop to remind people that life is not about trying to impress others. The rest of the album includes guest appearances by Jay Bizzy, Mic Boyd, Jordan Croucher, Preacher K, White Mic and more. Four singles have been released off the album: "Find Out" (which won the 2007 East Coast Music Award for Best Rap/Hip-Hop Single), "Feelin' Fine Remix", "All About U", and "Hard to Be Hip Hop". Hitch Hikin' Music also received a Juno Award nomination for Rap Recording of the Year in 2007.

Classified enlisted the help of fellow Nova Scotia native Joel Roy to beatbox during some of his songs. The actual singles that Roy beatboxed for are unknown but it is believed that he can be heard in the single "The Maritimes".

In early 2009, the hit single "Anybody Listening" brought Classified to mainstream success as it peaked at #52 on the Canadian Hot 100 and the music video received heavy rotation on MuchMusic. Classified's thirteenth studio album, Self Explanatory received highly positive reviews from the critics and debuted on the Canadian Albums Chart at #25 making it Classified's first album on that chart. At the 2009 MuchMusic Video Awards on May 21, 2009, Classified won the MuchVibe "Best Hip-Hop Video of the Year" award for "Anybody Listening" directed by Harv Glazer and produced by Robert Wilson of TwoThreeFiveFilms. Off Self Explanatory, Classified would enjoy more mainstream success in early 2010 with another hit single, "Oh...Canada" peaking at #14 on the Canadian Hot 100 and was certified platinum in digital downloads by the CRIA. Also in early 2010, Classified received three Juno Award nominations, which was for Rap Recording of the Year, Single of the Year, and Video of the Year. In early 2011, "Oh...Canada" received a Juno nomination for "Single of the Year".

On March 22, 2011, Classified released his fourteenth album, though it was only his second major studio album, Handshakes and Middle Fingers. The first single off the album, "That Ain't Classy" reached #45 on the Canadian Hot 100. The album debuted at #7 on the Canadian Albums Chart, making it his highest charting album to date.

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