He subsequently recorded his debut album Jelleestone Thirteen, which was produced by Jon Levine of The Philosopher Kings. He was preparing to release the album on his own independent label Rex Entertainment, but began attracting label interest in the United States after Nelly Furtado, who had the same manager, began talking about his work in media interviews. Signed to Warner Bros. Records in 2000, he released Jelleestone Thirteen on the label in 2001. The album's single, "Money (Part 1)", was a top 40 hit in Canada and reached #75 on Billboard's Hot Singles Sales chart.
In June 2003, Carty and his cousin David Gayle were arrested outside The Money nightclub in downtown Toronto, after an altercation in which he was alleged to have threatened another man, during which Gayle was discovered to have a gun hidden in his shoe. Testimony during the trial revealed that the plaintiff, not Carty, had initiated the incident after he felt "brushed off" by Carty, and that Carty had no knowledge of Gayle's gun. Gayle was sentenced to 15 months in jail, while the charges against Carty were dropped.