Rockland was the second of three Rockland brothers to join the gay porn industry, following in the footsteps of his older brother, Vince Rockland. The eldest brother, Shane Rockland, joined the industry later. All three appeared together in the 1996 gay porn film, Three Brothers.
He was the winner of the 1994 Best Newcomer by the Gay Erotic Video Awards and winner of 1995 Best Newcomer by the Grabby Awards for his role in Flashpoint.