<Li> Sean Penn as David Kleinfeld . For the pivotal role of Carlito's sleazy lawyer and best friend, Penn was lured back from early retirement by the challenge of playing the corrupt lawyer . Taking the role meant that he could finance his movie The Crossing Guard and work with Pacino . De Palma and Penn sat down and discussed what' 70s mob lawyers looked like . Often, men in the entertainment business can look more bizarre than the talent they represent . Penn 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 attempting to look like him, threatened the filmmakers with a defamation lawsuit . </Li> <Li> Penelope Ann Miller as Gail . Carlito's girlfriend and one of the few people he truly trusts, she is the only person who has ever seen Carlito's goodness . She is a dancer dreaming of the big time, but is reduced to working in a strip club to make ends meet . Although the story is a suspenseful crime thriller, their doomed romance is at the heart of the film . At the time, Miller was 29 years old to Pacino's 53 . Casting for Gail proved difficult because of the character's striptease scenes . The character needed someone who was both a talented dancer and actor . </Li> <Li> John Leguizamo as Benny Blanco . Leguizamo completed the main cast as "Benny Blanco from the Bronx", an up - and - coming gangster who is determined to exceed Carlito's reputation but lacks any sense of ethics . </Li> <Li> Luis Guzmán as Pachanga . One of the few remaining old time friends of Carlito, he works as his right - hand man at the Club Paradise . He would eventually betray Carlito to work with Blanco . After Carlito escapes and kills the mobsters, Pachanga and Carlito run to Gail and the train, where Blanco shoots both Carlito and Pachanga . In Koepp's first draft of the screenplay, Pachanga spoke in a very heavy slang style . Following rumbles from the Latino cast and crew, Koepp toned this down . </Li>

Who plays benny blanco in carlito's way