Penelope Ann Miller, 29 and topless

Penelope Ann Miller in Carlito’s Way (1993)

Carlito’s Way is a stylish Brian de Palma piece about a drug dealer named Carlito who is released back into society on a legal technicality, and intends to use this God-sent serendipity to start a completely new life – an honest life away from the rackets. It is based upon two realistic books (Carlito’s Way and its sequel, After Hours) by a guy who grew up in the Puerto Rican barrios of New York, and later became a judge.

One of the most interesting things about the movie is that it is essentially a familiar western plot, except that it takes place outside of the Old West. Carlito is like a legendary gunslinger who sets down his weapon, then finds that he can’t run from his reputation. Every guy who wants to be known as the fastest gun in the West either wants to kill him or hang with him. All of the men he has ever known are deeply involved in the criminal life, and it’s a struggle to make a few honest bucks so he can fly away and open his rental car agency on the islands.

It’s a very good movie, featuring the usual fine performances from Sean Penn and Al Pacino, with a taut chase scene at the end though the New York subways and Grand Central Station. Not the least of the visual splendors in the movie was Penelope Ann Miller as Carlito’s girlfriend. There is a sexy “staged voyeur” scene in Carlito’s Way which rivals the one in Body Heat. Miller lets Pacino watch her through her chained door opening. She removes enough clothing, and teases him enough, to get him to break in.

This film is rarely mentioned as one of Brian DePalma’s directing successes or as one of Al Pacino’s memorable roles, but I think it belongs on both lists, and I think IMDb members have it pegged quite well as a near-classic.