In 1997, Jason released his first LP, Eye & I, with the assistance of the Capitol Hill Music label. Music critics gave the album high scores. Allmusic commended the rapper’s ability to mix such styles as soul, dancehall, reggae, and hip-hop in all 20 tracks of the album. The LP didn’t become too commercial successful in Canada because songs weren’t played on radio stations. However, it still managed to sell over 4,000 copies in three months.
In 1999, the rapper recorded a single “And What?” with the assistance of Saukrates.
In 2000, the artist released an EP, Husslin', after getting support from Figure IV Entertainment. In the USA, the album was promoted by Fat Beats Records. The leading track “Husslin” reached the 41st spot on Canadian Hot 100.
The singles "Husslin" and "Mic THUGS" made it into the rapper’s second LP, Quest for Fire: Firestarter, Vol. 1., which came out in 2001. The album also featured such hits as "Ol 'Time Killin'" and "BaKardi Slang". Twenty-five thousand copies of the LP were sold within the year. The album earned positive reviews from the majority of critics. The Source magazine rated it as 3.5 out 5. Meanwhile, RapReviews.com gave it 7 out of 10.
After MCA label closed in 2003, the release of the next LP, Quest for Fire: Firestarter, Vol. 2, was delayed. Kardinal was left without a label, even though Timbaland and The Neptunes were ready to become producers. Later, the rapper released an independent mixtape, Kill Bloodclott Bill.
In 2005, Jason started working with EMI and Virgin Recordings. He released a new LP, Fire and Glory. The album featured such hits as "Everyday (Rudebwoy)" and "Heads Up". Critics gave high scores to the album. Singles reached high spots on the national chart. Many clubs tried to book Kardinal Offishall for private events, but it was rarely possible.
In 2008, the rapper released one more LP, Not 4 Sale with the assistance of Kon Live / Geffen Records. It was a huge success. The album featured five big hits, which made it into Billboard Hot 100. The top single "Dangerous”, recorded with Akon, became platinum. The album sold about 12,000 copies in just one week. Critics gave it excellent reviews. The LP earned a Juno Award for Rap Recording of the Year in 2009.
The same year, Lady Gaga invited Kardinal to record her song “Just Dance (RedOne Remix)". In 2010, he assisted Rahgav in recording “So Much”.
In 2012, the rapper presented his next LP, Allow Me to Re-Introduce Myself. It was recorded with an American hip-hop producer Nottz. The album was available for free downloading at the artist’s official website.
In 2015, Kardinal recorded Kardi Gras, Vol. 1: The Clash. The LP featured a hit single, "That Chick Right There". It reached the 68th spot on Canadian Hot 100. However, the album itself didn’t make it into the charts.
In 2017, together with Сelebrity Maurauders and Joey Montana & Pree, the artist recorded a popular single “Winners”.
Kardinal Offishall continues recording hits and performs live.
