Andrew Fleming studied filmmaking at New York University's prestigious film school, where one of his three award-winning student films earned him a fellowship at Warner Bros. He co-wrote the screenplay for his feature film-directing debut, Bad Dreams (1988), about a young girl who survives the mass suicide of a cult group, but stays in a coma for thirteen years. Fleming later acknowledged that the film's gore was excessive and when he later made another thriller called The Craft (1996), he kept the gore to a minimum. For his second feature, Threesome (1994), Fleming was both director and sole screenwriter. Openly gay, Fleming wrote his story about three college students, with Stuart, played by Stephen Baldwin, falling in love with Alex (Lara Flynn Boyle), but Eddy (Josh Charles) finding himself attracted to Stuart.
Both of Fleming's first two films were largely ignored by the public, but The Craft, about high school witches, was a moderate success. His next film also followed the antics of high school students, this time two girls (Kirsten Dunst, Michelle Williams) who become secret advisers to President Nixon in Dick (1999). However, Fleming's first attempt at comedy didn't entice many moviegoers to the box office.
Fleming turned to television, directing the pilot of WB's Grosse Pointe and also serving as series producer before returning to the big screen to once again try his hand at comedy with The In-Laws (2003). Featuring a stellar cast that includes Michael Douglas, Albert Brooks and Candice Bergen, Fleming turned in his best work yet, creating a playful, hilarious comedy.