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Portrayed by: Ray Liotta
- Abusive Parents: Subverted, though Harry resents his father for beating him, to the audience it comes across more as tough love since the only time we see it happen is because Henry was cutting school to work at a place his father knew to be a hangout for hardened criminals.
- Alliterative Name: Henry Hill.
- Amazon Chaser: Henry doesn't take an interest in Karen until she chews him out for standing her for their double date with Tommy and her friend.
- 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.
- Consummate Liar: Henry lies to everybody. He lies to Karen constantly about the risks of the business and his infidelities. He tells Paulie he won't deal drugs and will report to him any of the crew who does... and then immediately brings Jimmy and Tommy in on a massive cocaine operation. He tells Jimmy he won't buy anything excessive with the money that'll draw attention. Gilligan Cut to Henry with a giant Christmas tree, shouting "KAREN! I GOT THE MOST EXPENSIVE ONE THEY HAD!!!!"
- Damn, It Feels Good to Be a Gangster : Provides the trope's quote. Hill enjoys the lavish lifestyle and respect from being a gangster.
- Drugs Are Bad: Not only does taking them make you dishevled and paranoid but selling them brings the heat of the FBI on you and drives away anybody that could have helped you.
- 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.
- Fatal Flaw: He's greedy and sets up own operation that gets him arrested. Worse is that he clearly hasn't learned anything by the end.
- It's All About Me: When Paulie begrudgingly gives Harry money despite him running a drug business behind Paulie's back, Harry's only thought is resentment for only being given a few thousand dollars after working for Paulie for so long. Even at the end, his only regret is that he has to give up the gangster lifestyle and live like a regular law-abiding citizen instead of being thankful for having escaped either imprisonment or mob retaliation. Especially since it was a fate he brought upon himself.
- Karma Houdini: Subverted Trope. Henry Hill avoids prosecution and mob retribution, but he will spend the rest of his life Brought Down To Normal, forever pining for the Glory Days.
- A Lighter Shade of Black: For all his flaws, he's not as sadistic as most of his fellow mobsters.
- Mr. Vice Guy: Henry cheats on his wife and his fatal flaw is his greed.
- Noble Demon: He's the most principled character throughout the movie, despite being an amoral criminal who'll play along with the rest of the crew.
- Nominal Hero: On the occasion he sticks up for someone, he'd be here.
- 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.
- Redemption Demotion: "Redemption" is debatable since Henry becomes a rat to save his own skin, and the only thing he regrets is getting caught.
- Sadist: Although less so than Jimmy and Tommy.
- Took a Level in Badass: Henry starts doing petty errands for the Mafia as a teenager. Some time afterwards, he's setting cars on fire.
- Took a Level in Jerkass: While he does become more badass, he also goes from a reasonably sweet kid to a complete thug.
- Used to Be a Sweet Kid: As a teen, Henry had a conscience. He still does as an adult, but by then he's not above threatening innocent people.
- Villain Protagonist: Since he's the main character, although he's also an Anti-Villain.
- Your Cheating Heart: Henry Hill abandons his family and moves with his mistress for a while. Paulie mildly calls him out on it. Henry's infidelity is a Berserk Button for Karen, at first.
Jimmy "The Gent" Conway
Portrayed by: Robert De Niro
- Ax-Crazy: Not as obvious as Tommy, but he does have some moments of mental instability.
- Badass in a Nice Suit: He may be a horrible boss as mentioned below, but it's hard not to admit he looks great in a suit,
- Bad Boss: Kills all of those who were involved in the Lufthansa Heist.
- This is ultimately his Fatal Flaw. Jimmy's inclination to whack any liability the second they stop being useful becomes pretty well spotted. As such, Henry and even Karen can tell they're being set up to be murdered, driving them both to forsake any loyalty to him and run to the FBI to rat.
- Big Bad: During 1980s.
- Blood Knight / Psycho for Hire: As mentioned during his introduction, Jimmy steals because he enjoys it. The profits it brings in are, in his mind, just an added bonu.s
- The Dragon: To Paul Cícero, despite not being a "made" man.
- Dragon-in-Chief: During 1980s.
- Even Evil Has Loved Ones: Jimmy cries when his best friend Tommy is murdered.
- Even Evil Has Standards: Jimmy gives Tommy a serious rebuke after the gratuitous shooting of Spider.
- Fatal Flaw: As mentioned above, his solution for any problem is to Kill 'em All. Forcing Henry to turn against him.
- Faux Affably Evil: He's capable of being polite to people, but at his core, he's an amoral thug.
- For the Evulz: Jimmy is into crime not out of greed but for the mere thrill of it all.
- Historical Villain Downgrade: The real Jimmy would sometimes lock children in refrigerators, murdered or had murdered even more people, and really did screw nearly everyone out of the Lufthansa heist.
- Laser-Guided Karma: When he is arrested by the end of the movie.
- No-Holds-Barred Beatdown: When he beats Billy Batts with Tommy.
- No Honor Among Thieves: After the Lufthansa heist, he begins murdering everyone who had something to do with it.
- The Obi-Wan: To young Henry. His advice is even sage like.Jimmy: Never rat on your friends and always keep your mouth shut.
- Soft-Spoken Sadist: He rarely raises his voice or threatens anyone. He doesn't have to.
Portrayed by: Joe Pesci
- 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: 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.
- Cold-Blooded Torture: Practically, the brutal murder of Billy Batts is this, especially considering that he did not die before Tommy killed him with a knife.
- Comedic Sociopath: At least In-Universe.
- Crazy Jealous Guy: Orders his girlfriend not to even speak to another man.
- Disproportionate Retribution: This is one of the reasons why Tommy performs many of his horrible actions.
- 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 him 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.
- Historical Villain Downgrade: The real Tommy de Simone was even more violent than his fictional counterpart and was a rapist, to boot.
- 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, Tommy De Simone, was a large, beefy guy. It's pointed out exactly once when he tells a story about being beaten by a cop: "Just once, I wish I was big!"
- Oh, Crap: When Tommy sees the room Tuddy is bringing him into is empty and realizes that his making ceremony is really a hit.
Portrayed by: Lorraine Bracco
- All Girls Want Bad Boys: Practically a poster child for this trope. As she puts it herself:Karen: I know there are women, like my best friends, who would have gotten out of there the minute their boyfriend gave them a gun to hide. But I didn't. I got to admit the truth. It turned me on.
- Historical Villain Downgrade: Karen is depicted as a faithful if aggravated wife in regards to Henry's constant affairs. In reality, she was also having affairs, in particular with Paulie.
- Jewish American Princess: Her parents are members of a country club, so she fits the trope.
- Narrator: She provides the wifes and girlfriends perspective of gangster life.
- Precision F-Strike: While avoiding any major swear words throughout the film, she lets out a religious exclamation at the top of her voice upon confronting one of Henry's mistresses over her apartment intercom by telling her to "Get your own Goddamn man!" The exclamation brings her to tears.
- Pretty in Mink: Wears a mink coat when she meets Henry when he's released from prison.
- She's Got Legs: As dark as the "Wake Up Henry" scene is, it's hard NOT to notice Lorraine Braco's legs in those short shorts of hers.
Portrayed by: Paul Sorvino
- Affably Evil: Comes off as a father figure
- Family Values Villain: He's a crime boss, but is a good husband and father.
- Horrible Judge of Character: He trusts Henry to tell him the truth explicitly, both in being in the drug trade or not and the whereabouts of Batts. Henry's lyng on both counts. When he finds out about Henry's drug business that was running behind Paulie's back, Paulie is legitimately heartbroken.
- Large and In Charge: Tall, heavyset, and a capo. It follows.
- The Leader: Of the Lucchese Family.
- Paul Cicero wasn't the leader of the Lucchese Family. He was a caporegime, which is a mid-level rank.
- 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
- Bullet Dancing: Subverted.