DeGrasso joined the veteran metal band Y&T in 1986, replacing their original drummer Leonard Haze. He remained with the group into the '90s. He would go on to play on Dave Mustaine's (Megadeth vocalist/guitarist) side project band, MD.45 in 1995. Mustaine asked him to join Megadeth in 1998 as drummer and continue the band's Cryptic Writings Tour. He was asked to play with Megadeth five days before the next show. He walked around with a walkman all day to memorize the songs. DeGrasso recorded and toured behind Megadeth's Risk album in 1999–2000, The World Needs A Hero in 2000–2001 and was featured on Megadeth's first ever live CD and DVD release, Rude Awakening in 2002.
Since Megadeth, DeGrasso has performed at the prestigious Modern Drummer Festival in 2002, Ultimate Drummers Weekend in Australia, Drummer Live in the United Kingdom and toured with Stone Sour (Slipknot vocalist Corey Taylor’s side project) and guitar legend Ronnie Montrose. Jimmy played with David Lee Roth Band in 2006 and joined with Ministry on their final tour in 2008. He is a highly sought after session player and drummer.