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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 disheveled 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.
- Historical Hero Upgrade: The closest the film version of Henry gets to killing someone is when he locks the front door of the restaurant during Billy Batts' murder. The real Henry Hill is known to have killed three people.
- 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.
- Jerkass Has a Point: He may have been cheating on Karen, but he had the right to be pissed when she pointed a gun in his face.
- 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.
- Narrator: Off the movie, obviously.
- 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.
- Rags to Riches: And back to rags again in the end.
- 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
- Affably Evil: Starts out as this, being an amoral thug who is also capable of being friendly and generous towards others. Becomes Faux Affably Evil after the Lufthansa heist.
- 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: After the Lufthansa Heist.
- The Dragon: To Paul Cícero, despite not being a "made" man.
- Dragon-in-Chief: By the end of the 1970s.
- The Dreaded: Just like his Real Life counterpart.
- Even Evil Has Loved Ones: Jimmy cries when his best friend Tommy is murdered.
- Even Evil Has Standards: Subverted. Jimmy gives Tommy a serious rebuke after the gratuitous shooting of Spider.....but mostly because they'll now have to dispose of the body.
- Fatal Flaw: As mentioned above, his solution for any problem is to Kill 'em All. Forcing Henry to turn against him when he realizes that he's become a liability.
- Faux Affably Evil: After the Lufthansa heist, being a remorseless sociopath who kills anyone who gets in his way while acting polite to lull them into a false sense of security. One of the biggest signs of the change is that he stops being generous.
- For the Evulz: Jimmy is into crime not out of greed but for the mere thrill of it all.
- Jerkass: Starts acting a lot more hostile after Tommy's death. Dropping most of his Faux Affably Evil traits and acts irritated all the time.
- 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.
- Lack of Empathy: Doesn't even care once about the loved ones of the victims his killing sprees leave behind (like Morrie's wife).
- Laser-Guided Karma: Is overjoyed to hear that Tommy is being made since having a made man in their crew guarantees them the protection and influence of the mafia, essentially allowing them to steal from and kill anyone who isn't made without consequence. But then he and Harry find out the whole thing was a setup to kill Tommy in retaliation for the murder of Billy Batts. And because Batts was a made man and they weren't, there's nothing they can do in retaliation.
- Nice to the Waiter: He is quite generous with his tips.
- 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.
- 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 bonus.
- Sadist: not as much as Tommy, but still a big one.
- The Sociopath: If the rest of the page is no indicator.
- Soft-Spoken Sadist: He rarely raises his voice or threatens anyone. He doesn't have to.
- Took a Level in Jerkass: Becomes more ruthless and unpleasant after the Lufthansa Heist.
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?"
- Badass in a Nice Suit: Being a violent sociopath doesn't stop him from dressing up tight.
- 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.
- Blood Knight: And loves to boast about it.
- Big Bad: During the 1970s.
- Brooklyn Rage: He's from Brooklyn and his Hair-Trigger Temper is legendary.
- Character Death: Gets whacked because of the murder of Billy Batts.
- 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.
- Deadpan Snarker: Well yeah, he is a funny guy after all.
- Disproportionate Retribution: This is one of the reasons why Tommy performs many of his horrible actions.
- The Dreaded: Big time, even to his friends. Just look at how silent Henry and company went when they thought he got angry with Henry.
- 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: Generally acts unpleasantly and like he's always pissed off.
- Karmic Death: He killed a made man before and is now killed when he thinks he is going to be "made" or become a prominent member of the Mafia.
- Kick the Dog: His treatment of Spider.
- Laughably Evil: Tommy really is a funny guy....EXCEPT when you say so to his face.
- 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.
- Old Shame: He is embarrassed by the fact that he was a shoe shine boy when he was a kid. Bringing this up is guaranteed to piss him off big time.
- Psycho for Hire: Essentially nothing more than a vicious underling of Jimmy.
- Rags to Riches: His background isn't explored in depth, but it's likely that his family wasn't particularly well-off either.
- Sadist: Very sadistic when you provoke him.
- Sir Swears-a-Lot: It's Joe Pesci, after all.
- The Sociopath: Theft, abuse, torture, murder, you name it, he's done it.
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.
- Berserk Button: Henry's infidelities. Finding out about his first infidelity has her harass his (first) mistress and aim a gun in her husband's face.
- Clingy Jealous Girl: Bordering on yandere levels. She pointed a gun in Henry's face when she found out he was cheating on her.
- 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 wives 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, especially to Henry.
- Even Evil Has Standards: Does not approve of Henry dealing drugs.
- 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: Subverted. 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
- Alas, Poor Villain: Sure, he is a criminal himself, but seeing him brutally killed over such a petty reason....
- Alliterative Name: Billy Batts.
- Asshole Victim: He may have taken his ribbing of Tommy too far, but it's not really a valid reason for Tommy (and Jimmy) to brutally murder him.
- Character Death: He is brutally killed by Tommy.
- Smug Snake: He's a made guy and you can tell he acts as though it means he can do or say anything. He goes well out of his way to push Tommy's buttons, thinking that his status will scare Tommy and Jimmy enough not to retaliate. He's wrong.
Portrayed by: Michael Imperioli
- Bullet Dancing: Subverted.
- Butt Monkey: Appears in two scenes, in one he is injured, in the other killed.
- Character Death: Killed by Tommy because he dared to talk back.
- The Chew Toy: In-Universe is seen like this.
- Precision F-Strike: "Why don't you go fuck yourself, Tommy?" Doubles as Famous Last Words.
- Sacrificial Lamb: Spider's murder at the hands of Tommy doesn't add any foreshadowing or any symbolism. Apparently, his death only serves another highlight or reminder of Tommy's murderous rage and poor temper control.