Pfeiffer began his music career in the mid 1980s, when, as a teen, he was a part of a thrash metal band called Beyond Death. The band's two other members went on to found the death metal band Cannibal Corpse in 1988. In 1994, Pfeiffer became a founding member and drummer of Goldfinger. He married Vicky Anderson, the band's Canadian publicist, in 1998. (Anderson left Universal Music in 1998. The couple divorced in 2011). In 2002, Pfeiffer moved from Los Angeles to his wife's hometown of Toronto. There, he started managing and producing punk bands. In 2005, Pfeiffer became an on-air host for 102.1 The Edge. Late in 2005, the Pfeiffers started their own record label, High 4 Records. Their first signing was Crush Luther whose self-titled CD was released on 13 February 2007. The next band to sign, Cauterize released the CD, Disguises, on 12 June 2007. He has also played with the CanadianRock Band, "The Salads". Pfeiffer is known to play sets wearing a thong and shows it to the crowd when Goldfinger covers Sisqo's Thong Song. At some shows, there is a band ritual where Goldfinger picks out a "lucky" audience member from the crowd to come up on stage. Once on stage, the audience member will bite off a piece of a Twinkie held between Pfeiffer's buttocks. Pfeiffer is a fan of ice hockey and states Wayne Gretzky would be the only man he would ever sleep with. Pfeiffer has performed an acoustic love song/tribute to a life-sized cardboard cut out of Wayne Gretzky mid way through a Goldfinger set. The song includes lines such as,
"Wayne Gretzky. I think he's kinda sexy, and maybe he'd be attracted to me; Darrin Pfeiffer, a stupid American boy. Wayne Gretzky; a handsome Canadian man."
Pfeiffer has released two albums under his alias "Dangerous Darrin". One is The Revenge...of Chicken McNuggets and the other, The Artist...Currently Known as Dangerous Darrin. They are sold at Goldfinger concerts and through Pfeiffer's website. Pfeiffer manages Diana Salvatore.