He started rapping at the age of eight and was winning competitions by the time he was 12. At age 14, he performed live on stage for the first time, with Nelson Mandela in attendance during Mandela’s first visit to Toronto following his release from prison earlier that year (1990). By 1993, he decided to change his alias “KoolAid”, and went by the moniker “Kardinal Offishall” after being inspired by the great 17th century French politician Cardinal Richelieu. That year, Offishall co-founded The Circle, a collective of artists including Choclair, Jully Black, Solitair, Tara Chase, and Saukrates. In 1994, he made his first recorded appearance on Saukrates’ single “Still Caught Up”.

Kardinal was signed to a publishing deal with Warner/Chappell Music Canada at the age of 20. In 1996, he released his first single “Naughty Dread”, which was featured on the Rap Essentials Volume One compilation and earned him a Juno Award nomination for Best Rap Recording. In 1997, Kardinal released his debut album Eye & I on Capitol Hill Music. The only single from the album, “On wit da Show”, had considerable video play on MuchMusic. The album received rave reviews from music critics. AllMusic stated that Kardinal “blended soul, dancehall, reggae, hip-hop, and a wholly inventive approach to beats on his 20-track debut album, Eye & I.” Unfortunately, the album was poorly distributed in Canada, and a lack of radio support resulted in the album receiving limited commercial attention. Over 4,000 copies of the album were sold in its first three months of release. In 1998, he was featured on the Juno-winning single “Northern Touch” with the Rascalz, Choclair, Checkmate and Thrust. The following year, he produced Choclair’s hit single “Let’s Ride”.

Husslin’ was an EP released on April 11, 2000. It was released independently on Figure IV Entertainment and distributed by Fat Beats Records in the United States. The title track, “Husslin'”, was one of the hottest 12″ singles of 2000. “And What?”, featuring Saukrates, was released as a single in 1999. “Husslin'” and “Mic T.H.U.G.S.” also appear on Kardinal’s second studio album, Quest for Fire: Firestarter, Vol. 1. An updated version of “U R Ghetto When”, known as “U R Ghetto 2002”, is on the Quest for Fire album. In 2000, Kardinal signed with MCA Records. He released the album Quest for Fire: Firestarter, Vol. 1 in 2001, which spawned the hits “BaKardi Slang” and “Ol’ Time Killin'”.One year after its release, 25,000 copies of the album were sold in Canada. It received generally favorable reviews from music critics. The Source gave the album 3½ out of 5 mics. RapReviews.com gave it a 7/10 rating, calling it a “mixed bag,” and stating “there are also some perfect 10’s to be found here.” The A.V. Club gave the album a favorable review, praising its “impressive musical and lyrical consistency.” AllMusic gave it 2½ out of 5 stars, noting that Kardinal “displays only flashes of promise here.” The album was nominated for Best Rap Recording at the 2002 Juno Awards.

After MCA folded in 2003, Kardinal’s highly anticipated follow up album Firestarter Vol. 2: The F-Word Theory was shelved along with the music video for the single “Belly Dancer” featuring Pharrell, and Kardinal eventually found himself without a label. Had the album been released, there would have been production from Timbaland and The Neptunes, among others.

In 2004, Kardinal released an independent mixtape titled Kill Bloodclott Bill with his production company, Black Jays, and he also released his second major-label album titled Fire and Glory on November 15, 2005, through Virgin Records in Canada only. Hits on Fire and Glory include “Everyday (Rudebwoy)” and “Heads Up”. RapReviews.com gave the album an 8.5/10 rating, stating “Fire and Glory is a better album than Firestarter Vol. 1,” and “aside from having better lyrics than most of his counterparts, Kardinal’s unique style also sets him apart.” The album was nominated for Rap Recording of the Year at the 2006 Juno Awards.

In 2008, he was featured on the Just Dance (RedOne Remix) by Lady Gaga, part of the EP “Just Dance (Remixes, Pt. 2)”. In 2010, he was included in the Young Artists for Haiti’s version of “Wavin’ Flag” in an effort to raise money for disaster relief. He starred along with many Canadian stars. Also in 2010, he was featured in Raghav’s single “So Much”. In 2011, he collaborated with Canadian dance-pop act Audio Playground on their gold selling single “Famous”, which reached #28 in Canada and #10 on the USA Billboard Dance charts. In 2011, he collaborated with singer Karl Wolf on his single “Ghetto Love”.

In 2013, Kardinal Offishall, along with Madchild from Swollen Members, were featured on Canadian hip hop artist Classified’s self-titled album on the track “Look Up”. He also appeared on the charity single “True Colors” by Artists Against Bullying. On December 16, 2013, Offishall joined Universal Music Canada as Creative Executive Director of A&R. Aside from developing Canadian talent, he has also expressed interest in developing international talent, stating “I’m searching the world for superstars.” On October 30, 2015, Kardinal Offishall released his fifth studio album Kardi Gras, Vol. 1: The Clash which spawned the hit single “That Chick Right There”, which reached number 68 on the Canadian Hot 100.

On June 4, 2019, Kardinal Offishall released a new single called “Run” which was used as the Toronto Raptors theme song during their championship run in the 2019 NBA Finals and also serves as the first single off his upcoming album Pick Your Poison.