Date: May 15, 1998

The Moment: Academy Award-nominee and Hollywood royalty actor Warren Beatty writes, produces, consults with Suge Knight on, and directs a movie about a California Senator who goes off the rails, beginning to speak his mind and truth to his own power, in the form of cringe-inducing raps, with an all-star rap soundtrack released by Interscope.

The Impact: Like the titular character, the movie was initially seen as a curious and naive attempt by old white Hollywood to reach out to young urban America, both by Beatty's Hollywood peers and casual viewers alike. As it turned out, both parties ended up loving it: Critics gave it generally positive reviews, the soundtrack produced one of the bigger hits of that summer (in the form of Pras, ODB, and Mya's "Ghetto Supastar"), and the unlikely cultural crossover actually, oddly, managed to work out.

The Upshot: While it hasn't aged so well and still can lay claim to one of the most universally reviled endings in '90s movie history, the film grossed $29 million worldwide, and picked up a handful of nominations for Beatty and Jeremy Pikser's screenplay (which only won a minor L.A. critics award, losing out almost universally to Shakespeare in Love or The Truman Show). The soundtrack was certified platinum by the RIAA. The movie was one of Warren Beatty's last great works, as he continues to ease off major projects. A white person would not go on to rap in such a massive film until 8 Mile arrived in 2002.