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1* ActorInspiredElement[=/=]DyeingForYourArt:
2** It was Creator/SeanPenn's idea to shave a receding hairline into Kleinfeld's head.
3** It was Creator/AlPacino's idea for Carlito to have a beard.
4* CastTheExpert: Frank Minucci really used to be a mobster before becoming a Born-Again Christian. Hence why he's so convincing as Tony Taglialucci.
5* FakeNationality:
6** The Italian-American Al Pacino is once again playing a (Mestizo) Hispanic gangster.
7** Likewise, Danish-American Creator/ViggoMortensen plays a Hispanic gangster.
8** Iranian-American Creator/AdrianPasdar plays the Italian-American Frankie Taglialucci.
9* HarpoDoesSomethingFunny: Creator/JohnLeguizamo improvised many of his lines. He actually turned down the role four times and only accepted when he was allowed to ad-lib.
10* HeyItsThatPlace: The exterior of the hospital where Carlito visits his bedridden attorney is the same one where Vito Corleone is taken in ''Film/TheGodfather''.
11* HostilityOnTheSet: Creator/JohnLeguizamo revealed in his autobiography that he and Penelope Ann Miller did not get along during filming. He claims he got revenge on her by having the wardrobe department take in her clothes an inch at a time causing Miller to go on a crash diet.
12* IronyAsSheIsCast: Carlito mentions in his mocking speech upon his release that he's "born again". Frank Minucci (Tony T.), a Born-Again Christian, used to be a gangster.
13* OneForTheMoneyOneForTheArt: Creator/SeanPenn took the role of David Kleinfeld just for the money so he could use it to fund his second film ''Film/TheCrossingGuard''.
14* ProductionPosse: Creator/BrianDePalma reused several actors from ''Film/Scarface1983'': Creator/AlPacino, Al Israel, Ángel Salazar, Jorge Porcel, Michael P. Moran, and Caesar Cordova.
15* ReferencedBy: Carlito's line "Here comes the pain!" was [[{{Sampling}} sampled]] in Music/{{Slipknot}}'s song "[[Music/SlipknotAlbum (sic)]]".
16* RomanceOnTheSet: Creator/AlPacino and Penelope Ann Miller became romantically involved during filming. Miller spoke publicly about their romance in interviews. But Pacino was in a relationship with Lyndall Hobbs at the time. Pacino attended the film's premiere with Hobbs and avoided Miller entirely.
17* WagTheDirector: According to Creator/BrianDePalma, Creator/SeanPenn demanded 30 takes of the shot of Kleinfeld asking Carlito to help him with Tony T's escape. When De Palma wanted to move on to the next shot, Penn screamed at De Palma. He continued to yell at De Palma on the ride back to New York City. He later called De Palma on the phone to continue yelling at him. De Palma said that was the only argument they had on the film.
18* WhatCouldHaveBeen:
19** Creator/AlPacino first envisioned Carlito with a ponytail, but after his visits to Harlem, he quickly realized the guys there were not into wearing their hair that way.
20** Pachanga's lines were originally written in phonetically spelled, heavily accented slang. But some of the crew members of Latino descent were offended by this. Creator/DavidKoepp rewrote Pachanga's lines in standard English and Luis Guzmán was directed to speak with a heavy accent and improvise some slang.
21** Creator/CharlieSheen and Creator/JohnTurturro were considered for David Kleinfeld. At an early stage, Creator/MarlonBrando was to play the role.
22** Creator/BrianDePalma wanted to shoot the climax of the film at the World Trade Center in New York but it was the target of a bombing, and he had to shoot it in "another railway station again." (De Palma's ''Film/TheUntouchables'' also featured a scene at a railway station.)
23** Creator/AbelFerrara was considered to direct.
24* YouLookFamiliar: The actors portraying Pachanga, Valentin (Norwalk's detective partner) and Rudy (the waiter at Carlito's club) have other roles in the 2005 prequel. Luis Guzmán's role is most prominent and he plays a similar character, a gruff assassin named Nacho.

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