I felt like I was too young, and I didn’t have anything to make movies about. So very specifically, I went to Pomona to get a liberal arts education and not do filmmaking, even though I knew that was what I ultimately wanted to do.
— Taylor, in a 2005 interview for Pomona College Magazine
Taylor began working for Cannon Films in 1987. After visiting China on an Avery Foundation grant, Taylor returned to L.A. and spent three years working with Ivan Passer; he also worked for Devon Foster, a director at HBO, as Foster's assistant.
Taylor met Payne while working temporary jobs in Los Angeles, eventually moving in with him for financial reasons. While roommates the two wrote short films and started writing Citizen Ruth. After winning money on the game show Wheel of Fortune, Taylor entered Tisch School of the Arts at the age of 30. He and Payne did further rewrites on Citizen Ruth while Taylor was a graduate student; the film got made during his third year there. Taylor received an M.F.A. in Filmmaking from New York University in 1996.