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Portrayed by: Ray Liotta
- Anti-Villain: Henry is more sympathetic than Tommy and Jimmy and provides A Lighter Shade of Black. His moral fiber is not that flexible when compared to the rest of his partners. It's established early on, during his teenage years, when he helps to bandage the arm of a man who had been shot and is berated for wasting good aprons.
- Badass in a Nice Suit: A semi-expository scene has Henry suiting up, which is warily received by his mother: "You look like a gangster!"
- Berserk Button: It was pressed hard when Karen's neighbor sexually assaulted her.
- Break the Haughty: When Henry realizes that he's going to get whacked he doesn't take it well.
- Damn It Feels Good to Be a Gangster: Provides the trope's quote. Hill enjoys the lavish lifestyle and respect from being a gangster.
- Even Evil Has Standards: Henry's a jerk and lifelong criminal, but draws the line at murder. Even he's visibly disturbed when Tommy and Jimmy brutally beat up Billy Batts.
- No Honor Among Thieves: Rats out all of his former associates as a plea bargain to avoid jail time. And being whacked by said associates.
- Properly Paranoid: While being hooked on drugs makes him overly manic, a lot of Henry's paranoia towards Jimmy and the Cops turns out to be valid.
Jimmy "The Gent" Conway
- Ax-Crazy: Not as obvious as Tommy, but he does have some moments of mental instability.
- For the Evulz: Jimmy is into crime not out of greed but for the mere thrill of it all.
- Alas, Poor Villain: When he realizes too late he's gotta answer for what he did to Billy Batts...
- Asshole Victim: Even Henry did not look so sad when he learns of his death.
- Ax-Crazy: And how. He is violent, irrational, paranoid, brutal and sadistic in the most frightening way possible.
- Badass Boast: After killing Spider, Tommy tries to use the line "I'm a good shot" as one. It doesn't fly, as there is nothing badass to brag about. Even one generic mobster is unafraid to call it out: "How could you miss at this distance?"
- Berserk Button: Almost anything, but special mention goes to Billy Batts tells him to "Go get your shinebox." The beating he gave Batts looked like it almost brought him to tears.
- Even Bad Men Love Their Mamas: He shows at least a trace of humanity thanks to his relationship with his mother.
- Fatal Flaw: His inability to control his temper ended up getting killed.
- Hair-Trigger Temper: He shot a guy in the foot for getting him the wrong drink, and later killed the guy by shooting him again. He also killed a made man just for insulting him at his birthday party.
- Jerkass: To the point of being a sociopath.
- Kick the Dog: His treatment of Spider.
- The Millstone: Most of the trouble the main characters get into is because Tommy would shoot anybody for so much as looking at him funny.
- The Napoleon: By default due to Pesci's actual stature. The real-life inspiration was a large, beefy guy.
Portrayed by: Lorraine Bracco
- Pretty in Mink: Wears a mink coat when she meets Henry when he's released from prison.
Portrayed by: Paul Sorvino
- The Leader: Of the Lucchese Family.
- Parental Substitute: Henry sees Paul as a better father figure than his own father. When Paul disowns him for lying about his drug deals, it became one of the few key factors that caused Henry to rat.
Portrayed by: Frank Vincent