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Played by: Adam SandlerA 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 bad he is at times: he cheats the Ethiopian miners out of thousands, cheats on his wife, and is completely selfish and estranged from his family.
- Badass Boast: "This is me. This is how I win."
- 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. 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.
- 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.
- 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.
- Kavorka Man: He's a balding middle-aged man with a beautiful wife (who can still fit into her dress that she wore when she was thirteen),
- 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 to bail him out of trouble several times.
- 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.
- 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.
Played by: Idina MenzelHoward 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...
Played by: Julia FoxHoward'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.
- MayDecember 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.
Played by: Kevin GarnettA 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.
Played by: Lakeith StanfieldHoward'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.
Played by: Eric BogosianHoward'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.
- 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.
- 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, tryingand failingto 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.
- 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.
- Bigger Bad: Phil is ultimately revealed to be this to Arno. Arno is actually mildly relieved and takes being locked in the faulty door much better than Phil, which ultimately results in his death.
- 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.
- 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 kills him at the end.
- 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.
- 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.
- Hero Killer: Phil murders Howard in cold blood right when it seems he's finally won.
- Karma Houdini: Most likely averted. 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, and Dinah has already sent cops on the way.
- Kosher Nostra: They're a pair of Jewish-American thugs.
- 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.
- 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.