He attended and graduated from Monsignor Bonner High School in 1988.
After high school, Kennedy began his career as a Hollywood extra. When Kennedy first arrived in Los Angeles, he became a professional Hollywood extra. A., he was reading a Joan Rivers autobiography in a diner when the waiter explained to him that he had been in a dozen movies as an extra.
Kennedy lent his voice to the videogame ESPN NFL 2K5 as a celebrity adversary with his own football team, the Upper Darby Cheesesteaks.
He is also unlockable as a free agent tight end in season mode.
In April 2010, sources reported that Kennedy would very likely return to the Scream franchise to star in the fourth installment; On December 31, 2012 Kennedy hosted and produced First Night 2013 with Jamie Kennedy, a New Year's Eve television special widely considered one of the worst shows of all time.