4. Carlito's Way (1993)
Carlito's Way perhaps doesn't get quite as much consideration as a bonafide classic as its gangster movie counterparts, but Brian De Palma's movie is undoubtably a good one: gripping plot, handsome direction and memorable characters make that so. The plot concerns Carlito Brigante (Al Pacino), a former criminal who is released from prison with plans to retire in paradise. This doesn't happen, though, as he's brought back into the shady dealings that he so wishes to avoid.
The Influence? Undeniably, the character of Ken Rosenberg in
Vice City is an obvious homage to Sean Penn's character, David Kleinfeld, in
Carlito's Way. Despite the fact that they've been made to look extremely similar, they're both addicted to cocaine. Rosenberg's office also seems to have been based on Kleinfeld's, too. The story itself, with Tommy Vercetti coming out of prison without ratting on anybody, is also comparable to that in
Carlito's Way.