The 1993 American crime drama film "Carlito's Way" was directed by Brian De Palma and written by David Koepp, based on the novels "Carlito's Way" (1975) and "After Hours" (1979) by Judge Edwin Torres. It stars Al Pacino, Sean Penn, Penelope Ann Miller, Luis Guzman, John Leguizamo, Jorge Porcel, Joseph Siravo, and Viggo Mortensen.

Pacino plays Carlito Brigante, a Nuyorican criminal who vows to go straight and to retire in paradise. His criminal past however proves difficult to escape; he unwillingly ends up being dragged back into the same activities that got him imprisoned. As Dave Kleinfeld, Penn has a pivotal role. He is Carlito's sleazy lawyer and best friend.

To play the role, Penn was lured out of early retirement by the challenge of playing the corrupt lawyer. Taking the role meant that Penn could finance his movie "The Crossing Guard" (1995) and work with Pacino. De Palma and Penn discussed what 1970s mob lawyers were known to look like. Penn then shaved the hair on the front of his forehead to give the appearance of a receding hairline; he permed the rest. Alan Dershowitz, believing that Penn was trying to look like him, threatened the filmmakers with a defamation lawsuit.

"Carlito's Way" was released in November 1993. It initially received mixed reviews from critics and only did fair at the box office. Its popularity has since improved in the following years. It has gained a big cult following and is really considered one of De Palma’s most enduring films.

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