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     Howard Ratner
This is how I win!
Played by: Adam Sandler

A charismatic, impulsive jewelry store owner with an overwhelming gambling addiction.

  • Affably Evil: To the point that he's so affable that it can be easy to forget just how horrible of a person he is: he cheats the Ethiopian miners out of thousands, cheats on his wife, and is completely selfish and estranged from his family.
  • Alas, Poor Villain: While he was a gambling scumbag, he gets coldly shot by Phil right after he wins the biggest bet of his life. Arno is clearly shown to be appalled at his death, with himself getting shot by Phil after confronting him on it.
  • All for Nothing: Howard risks everything on one last wager. He manages to sneak the cash to his girlfriend, and his girlfriend evades the thugs to place the bet. He wins big, and his girlfriend gets the money, but it doesn't matter because Phil shoots and kills him moments after his victory.
  • Badass Boast: "This is me. This is how I win."
  • Boom, Headshot!: And right after winning the biggest bet of his life!
  • Bullying a Dragon: Howard spends the entire film inconveniencing, delaying or just plain irritating Arno's goon Phil in some way. This ultimately earns him a bullet to the face after he locked him up in his entrance.
  • Byronic Hero: Although lacking many of the "heroic" qualities, Howard does embody this trope: he has aggressive mood swings, he's Hot-Blooded, he's extremely charming and fast-talking but also completely senseless to the feelings of others, and he's obsessed with living life through his obsessive gambling and fixation on "winning".
  • Cheshire Cat Grin: Breaks into a big, toothy grin whenever he's sure of a bet.
  • The Chew Toy: He is the cause of all of his own misfortune, but he does lose constantly throughout the film. It's not Played for Laughs either. Even when he finally wins — huge — he gets killed moments later.
  • Classical Anti-Hero: Howard displays few positive qualities, being a sleazy adulterer and gambling addict who can't stop ruining his own life, but somehow you find yourself rooting for him as he struggles to scheme his way out of whatever hole he's dug himself into.
  • Complexity Addiction: As part of his gambling problem, Howard is obsessed with using convoluted moneymaking schemes to solve the problems, even when he could simply solve them by paying people who are literally standing in front of him.
  • Con Man: It turns out he payed the Ethiopian miners $100,000 for the opal which is merely a tenth of what he thought it was really worth. Soon after he continues to gamble using other peoples money and valuables.
  • Does This Remind You of Anything?: His reaction whenever he wins a bit is pretty much literally orgasmic.
  • Even Evil Has Loved Ones: Not exactly 'evil', but for all his criminal actions and faults, he does clearly love his family. Even after all he's done, Arno is shown to be devastated at his death.
  • Fatal Flaw: Howard's gambling addiction means he's constantly upping the stakes and doubling down, even though he has multiple opportunities to simply pay Arno and walk away.
  • Foot-Dragging Divorcee: Dinah hates him and wants to divorce him as soon as possible, but Howard keeps trying to delay it in the vain hope that he can work things out.
  • The Gambling Addict: The very platonic ideal of this trope. Howard's crippling gambling addiction basically causes all the problems in the film, costing him his marriage, multiple friendships and business partnerships, and ultimately his life.
  • Glad-to-Be-Alive Sex: Promises this to Julia after they win the bet and escape the gangsters. Unfortunately Howie gets his brains blown out before he can follow through.
  • Greedy Jew: Played with. He's a Jew and has a huge gambling addiction. But it's clear that his real problem is not greed, but rather that he's a thrill seeker who loves to gamble with other people's money.
  • The Hero Dies: Shot in the head seconds after winning the biggest bet of his life.
  • Jerkass: He's a pretty rancid individual with very little redeeming qualities. He lies, cheats, and manipulates his way throughout the film, with no regard for the suffering of others that his actions could cause.
  • Large Ham: What only Adam Sandler can do. Thanks to his acting, Howard appears very casual and offhanded even if his own life is jeopardized.
  • Karmic Death: Deserving or not, his gambling addiction and thrill-seeking behaviour ends up costing him his own life.
  • Kavorka Man: He's a balding middle-aged man with a beautiful wife (who can still fit into a dress that she wore when she was thirteen) and a much younger voluptuous mistress.
  • Manchild: Partially, and in a manner very different than Sandler's usual roles. He's short-sighted, throws temper tantrums when he doesn't get his way, and asks his father-in-law to bail him out of trouble several times.
  • Manipulative Bastard: Howard is pretty smooth-talking and charming. He convinces many people around him to either give him their valuables to gamble with or to use them as pawns in his money-making schemes, including his own friends and family.
  • No Social Skills: Downplayed. He's actually quite a talkative and charismatic guy, but he can't seem to resolve any disagreement at all without having a loud public screaming fit, often embarrassing his friends and family.
  • Post-Victory Collapse: Gets killed tight after he won the greatest bet of his life.
  • Sir Swears-a-Lot: Almost every other fuckin word that comes out of his fuckin mouth is fuck.
  • Smug Snake: All the way. He makes a ton of false promises with people and jeopardizes their valueables in bets or other schemes that he think will make him money and pay them back. Only problem is that everytime he is way overconfident in his schemes and constantly looses bets which results in nothing but pissing off the people he owes to and getting himself into more debts. And even when he does win (and would finally be able to pay off everyone he owes to) he gets shot in the face because he pissed off the wrong guys for too long.
  • Thrill Seeker: He could be the archetypal example. Howard literally can't help himself, because he has a pathological need to bet, which ultimately leads to his death.
  • Too Dumb to Live: Deconstructed. Howard is actually savvy and cunning when he needs to be and recognizes that he's way in over his head. It's not a lack of intelligence that continually lands him in hot water with Arno and the mob, rather his risk-seeking behavior and gambling addiction, which are shown to be deep-seated and compulsive. The end result is still the same, though.
  • Tragic Hero: Howard is a Thrill Seeker and a Gambling Addict, which unsurprisingly causes his demise in the ending.
  • Villain Protagonist: An egotistical opportunist who makes tons of false promises and screws everyone around him so he can make more bets.
  • Yank the Dog's Chain: He ultimately wins the biggest bet of his life, only to get shot and killed by Phil.
     Dinah Ratner
Played by: Idina Menzel
Howard Ratner's estranged wife, on the verge of divorcing him.

  • Hero Antagonist: As part of Howard's Moral Myopia. She's actually more or less right about everything: she can see that he's addicted, she's worried about his safety, and she knows that he cheated on her with Julia. But Howard's Moral Myopia makes her at least seem like a roadblock for her insistence on getting a divorce.
  • Jerkass Has a Point: She isn't that bad, but she's kind of a nag — except, if only she had got the police there earlier...
  • "The Reason You Suck" Speech: A very cold, casual one directed Howie's way.
    "Howard, I think you are the most annoying person I've ever met. I hate looking at you, I hate being with you, and if I had my way I'd never see you again."

Played by: Julia Fox
Howard's much younger girlfriend, and an employee at his store.
  • Aw, Look! They Really Do Love Each Other: Despite their fights and her ambiguous encounter with The Weeknd, Julia really does seem to love Howie, going so far as to get a tattoo of his name and risk her life to get him his money.
  • Book Dumb: Downplayed. While she appears to do what Howie wants most of the time, especially with regards to betting, her attempts to evade the gangsters by herself show that she and Howie make an excellent team.
  • Embarrassing Tattoo: After breaking up with Howard, she gets "Howie" tattooed on her ass to win him back. Even he is baffled by this.
  • Lovable Alpha Bitch: A non-high school example. Julia appears to be a materialistic, somewhat manipulative, and archetypal "trashy" person. However, her major turning point is her genuine devastation when Howie breaks up with her, and when Howie asks her to make an extremely risky bet, she lovingly and genuinely does so.
  • May–December Romance: She's maybe half Howard's age, but seems to be sincerely in love with him.
  • Meaningful Name: Julia's name is sometimes shortened to "Jules", which sounds exactly like "jewels". Quite appropriate for a materialistic young woman in a love affair with a jeweler.
  • Ms. Fanservice: Wears lingerie and briefly masturbates in one scene.
     Kevin Garnett
Played by: Kevin Garnett
A real-life member of the Boston Celtics.
  • As Himself: Kevin Garnett plays Kevin Garnett.
  • Bald of Awesome: As in real life.
  • Maybe Magic, Maybe Mundane: He views the opal as a good luck charm that guarantees him success on the court. No one else in the film gives any credence to this, but the film shows that he wins overwhelmingly when he has the opal in his possession and plays well below his standard when he doesn't.
  • What the Hell, Hero?: He points out to Howard that he finds it very nasty that Howard merely paid the poor Ethiopian miners $100 000 for the opal, when Howard thought that it was really worth a million but yet decided to be greedy and not give them the price he saw fitting.
Played by: Lakeith Stanfield
Howard's increasingly frustrated business partner.
  • Only Sane Man: Is naturally irritated by Howard psyching up Kevin Garnett over an opal he doesn't even plan on selling him when they could both easily earn a profit by selling him one of Demany's fake Rolexes.
  • Screw This, I'm Outta Here!: Breaks off his business partnership with Howard after learning Howie gave away some of the watches Demany wanted him to sell.
     Arno Moradian
Played by: Eric Bogosian
Howard's brother in law, to whom he owes a large sum of money.
  • Actually Pretty Funny: While his bodyguards aren't amused in the slightest, Arno can't help but smile and chuckle when Howard's wild bet on the Celtics pays off.
  • Alas, Poor Villain: In spite of everything, he becomes very upset when Phil kills his brother-in-law, which Arno didn’t think was deserving. After all he was his family. He tries to escape when Phil becomes hostile even towards his own boss, only to be shot by him as well.
  • Ambiguously Jewish: According to his actor, he's not Jewish by birth, but an Armenian-American who married into the family.
  • Big Bad: Howard's primary headache throughout the movie, as the loan shark he spends the whole running time trying to ward off. However this becomes increasingly subverted as his bodyguard Phil's patience wears thin and the mafioso becomes increasingly violent and insubordinate, ultimately reducing Arno to the role of a Big Bad Wannabe.
  • Big Bad Wannabe: As stated above, he becomes this particularly at the end of the film. Howard states that it's not Arno himself whom he is afraid of, only Nico and especially Phil, whom Arno relies to much on when it comes to intimidation. Phil turns out to be a Dragon-in-Chief who becomes fed up with his own boss and kills both him and The Hero in the end.
  • Even Evil Has Loved Ones: Besides being related to him through marriage, it becomes clear that Arno doesn't actually want to see Howard get hurt, trying—and failing—to keep his bodyguards from resorting to violence. When Phil ultimately snaps and shoots Howard, Arno is genuinely horrified.
  • Go-Karting with Bowser: Though the main antagonist, Arno is also Howard's brother-in-law, leading to awkward but civil interactions at family gatherings.
  • Kosher Nostra: He's technically not associated with any criminal organization (that we know of), but him being a loan shark and a Jewish convert qualifies him for this trope.
  • The Leader: Deconstructed. Arno is the head figure of his loan shark business, but he only have so much power as he relies too much on his henchmen when it comes to collect debts and intimidation tactics. On his own though, he isn't much of a threat as Howard points out. Arno's own henchmen Phil and Nico proves to not be so loyal to Arno as they eventually become fed up with their own boss and decides that they might as well kill Arno along with Howard and then proceed to make money on their own by looting Howard's store.
  • Loan Shark: His occupation. Howard has borrowed high amounts of money from Arno and is in great debt to him which is why Arno is his biggest headache throughout the movie.
  • No Respect Guy: While Arno has a threatening aura early on in the film, Howard rightly points out that he has much more bark than bite. His Jewish in-laws quietly disrespect him for being a Gentile, Howard doesn't take their business agreement seriously, and his goons use way more force than he wants them to. This culminates with Arno being shot by Phil shortly after Howard is killed.
  • Reasonable Authority Figure: Despite being a loan shark who keeps a pair of violent mafiosos on retainer, Arno gives Howard multiple opportunities to pay him back and discourages unnecessary violence. This backfires when Phil's patience finally gives out, earning both Howard and Arno himself bullets to the face.
  • The Unfavorite: Despite the fact that Howard is a completely reckless gambling addict (at best...) the much quieter and more subdued Arno is clearly left out of family gatherings because he's Armenian.
     Phil & Nico 
Played by: Keith Williams Richards (Phil) and Tommy Kominik (Nico)
Two brutal mobsters affiliated with Arno.
  • Ax-Crazy: Phil is clearly unafraid of violence, and when pushed too far he murders both Howard and Arno, his own boss, on pure impulse.
  • Bald of Evil: Nico.
  • Butt-Monkey: Nico in particular suffers from a lot of physical punishment; he gets punched in the face by one of Howard's guards, Howard deeply bites him in the arm during a fight, and is then locked in an incredibly hot glass room with Phil and Arno for hours.
  • Destination Defenestration: They threaten to drop Howard out of his office window after he reveals that he had their money but chose to bet it on the Celtics game.
  • Disproportionate Retribution: Phil kills Howard dead for stalling his time, then kills Arno for confronting him on it.
  • Dragon Ascendant: When Phil kills Arno, he seems to become this, ordering Nico around.
  • Dragon-in-Chief: Howard himself thinks that Arno is completely unintimidating without Phil. Phil indeed gets fed up with his boss and is the one to kill Howard and his own boss at the end.
  • Establishing Character Moment: His first scene has him meeting Howard. At first, he tries to be patient, but quickly loses his temper and slaps Howard in the face when he won't hurry.
  • Evil Is Petty: Phil kills Howard because he pissed him off. Then he also kills his own boss because he was mouthing off to him for killing Howard and trying to flee the scene.
  • Eviler Than Thou: He proves himself to be this when he shoots Howard out of sheer murderous impulse and his own boss approximately two seconds later when Arno starts to go "what the hell did you just do, man?".
  • Evil Sounds Deep: Phil has a pretty deep voice which adds to his intimidation.
  • Fat Bastard: Nico is noticeably heavier than anyone else in the film.
  • Flat Character: Nico is barely more than an extra, with all the real characterization going to Phil.
  • Greater-Scope Villain: Phil is ultimately revealed to be this to both Arno and Howard. Arno is actually mildly relieved and takes being locked in the faulty door much better than Phil, which ultimately results in his and Howard’s death.
  • Guttural Growler: Phil has a deep and raspy voice.
  • Hair-Trigger Temper: Phil especially. Howard eventually sends the mobster over the edge, with lethal results.
  • Hate Sink: Phil has little to no redeeming qualities — he's prone to violence, constantly harasses and antagonizes Howard, and even shoots Howard in the face moments after he wins big. After that he then kills Arno his own boss when he objected to Howard's death and tried to escape.
  • Hero Killer: Phil murders Howard in cold blood right when it seems he's finally won.
  • Karma Houdini: Ambiguous. The movie doesn't show them being apprehended for murdering Howard and Arno, and then looting the store, but they did so in full view of a security camera while leaving their fingerprints all over the shop, plus Dinah has already sent cops on the way.
  • Kosher Nostra: They're a pair of thugs working for a Jewish loan shark. However, Phil most likely isn't Jewish himself, given the fact that he wears a cross around his neck and is played by a non-Jewish-American actor. Nico might be though, as his actor is Jewish-American.
  • Offing the Annoyance: Phil kills Howard for locking him in the store entrance and forcing him and Arno to watch the game.
  • Rage Breaking Point: After spending the entire movie getting repeatedly deceived, attacked, and generally inconvenienced by Howard, Phil finally crosses it when Howard locks him, Nico, and Arno in the security entrance of the jewelry store for 3 hours and forces them to watch the Celtics game. Phil murders Howard the second he gets out, and then kills Arno just for objecting.
  • The Sociopath: Phil is easily the most evil one in the film, is prone to violence in almost every scene he is in, and is shown to have no sense of loyalty or respect as he remorselessly kills both Howard (right after he won the biggest bet of his life) and his own boss Arno for becoming upset and trying to escape.
  • Uncertain Doom: What happened to them isn't clear, but it doesn't look good. Howard and Arno both die at the hands of Phil's impulsive violence, which more or less seals the deal for them — they're last shown impulsively flinging Howard's watches into a bag, all caught on camera, and the police are coming thanks to Dinah. Whether that means death or prison, it's not good.
     The Weeknd 
Played by: The Weeknd
Real-life singer The Weeknd.

  • Adam Westing: The Weeknd acknowledges this as the case, saying that his sleazy behavior in the movie was representative of how he acted around 2012.

Played by: Judd Hirsch
Howard's father-in-law.

  • Obnoxious In-Laws: Averted. He's friendly towards Howard during Passover and even (albeit reluctantly) goes along with one of his schemes.