Drugstore Cowboy (1989)

A darkly funny, stylish, and realistic look at the world of drug addiction in 1971, Drugstore Cowboy focuses on Bob (Matt Dillon) as the leader of a bedraggled quartet of addicts - his frustrated wife Dianne (Kelly Lynch), his loyal partner Rick (James Le Gros), and Rick's girlfriend Nadine (Heather Graham) -- who get what they need by robbing drugstore pharmacy departments in the Pacific Northwest. The movie presents a rare insider's view of the drug lifestyle that is all the more refreshing for its lack of facile moralizing or apologies. It's a true comedy of desperation.

GoodFellas (1990)

Martin Scorsese's 1990 masterpiece GoodFellas immortalizes the hilarious, horrifying life of actual gangster Henry Hill (Ray Liotta), from his teen years on the streets of New York to his anonymous exile under the Witness Protection Program. The director's kinetic style is perfect for recounting Hill's ruthless rise to power in the 1950s as well as his drugged-out fall in the late 1970s.

Homegrown (1998)

A comedy-thriller about three experienced pot growers in northern California (Billy Bob Thornton, Hank Azaria, and Ryan Phillippe) who guard their valuable outdoor crop against raids by the cops and unwanted competitors. When their mysterious leader is apparently murdered, Thornton assumes the dead man's identity to arrange one last, lucrative bumper-crop deal, but pulling off the scam proves to be a lot harder than they'd anticipated.

Leaving Las Vegas (1995)

Ben (Nicolas Cage, in an Oscar-winning performance) is a former movie executive who's lost his wife and family in a sea of alcoholic self-destruction. He's come to Las Vegas literally to drink himself to death, and that's when he meets Sera (Elisabeth Shue), a prostitute who falls in love with him -- and he with her -- despite their mutual dead-end existence.

My Name is Bill W. (1989)

Based on the true story of Bill Wilson (James Woods), a successful stock broker whose life falls apart after the stock crash of the 20's must and come to grips with his alcoholism. He forms a support group with fellow drunk (James Garner) that would eventually become Alcoholic's Anonymous.