After making acclaimed student films at Harvard and at AFI film school, Brooklyn native Aronofsky began working on his first feature, Pi, in 1996. When he ran out of money midway through production, he and his producer asked everyone they knew to chip in $100 to help finish the project. A black-and-white brainteaser about mathematics and madness starring Aronofsky's Harvard classmate Sean Gullette, the film became an art house sensation upon its release in 1998. In 2000, Aronofsky followed up with a relentlessly grim adaptation of Hubert Selby Jr.'s novel Requiem for a Dream. The film put Aronofsky on the map with unspoken universal recognition as the Most Depressing Film Ever to Star a Wayans Brother.
Aronofsky's first foray into Hollywood filmmaking led to his first major letdown: In 2002, his big budget adaptation of The Fountain collapsed after Brad Pitt walked off the set. Half the movie's budget evaporated but Aronofsky stuck with it and six years after Requiem, the director released a Pitt-less version of the film starring Hugh Jackman. After being booed at the Venice Film Festival, Aronofsky rebounded in 2008 with the release of The Wrestler and Black Swan.
Aronofsky has a habit of getting his actors Oscars: Melissa Leo and Christian Bale were awarded for their efforts in The Fighter (which Aronofsky produced) and the very-pregnant Natalie Portman took home the top prize for Black Swan (Mickey Rourke, Marisa Tomei, and Ellen Burstyn will just have to be content with nominations). Aronofsky has yet to take one home himself.