Gannascoli received his "big break" in acting from Benicio del Toro, whom he met on the set on Money for Nothing.

He also introduced him to Sheila Jaffe and Georgianne Walken, who did casting work for the HBO TV series The Sopranos.

He later secured a recurring role as the nephew of Richie Aprile, Vito Spatafore, in the season two episode "The Happy Wanderer".

Along with Dan Grimaldi playing identical twins Patsy and Phillip "Philly Spoons" Parisi and Saundra Santiago playing identical twins Jeannie and Joannie Cusamano, it was one of the three times that the show used a single actor for separate roles.

Gannascoli brought the idea to the writers of making his character gay from a true story of the Gambino crime family, in a book called Murder Machine.