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  • Alternative Character Interpretation:
    • Did Jordan Belfort reform and repent of his actions at the end or is he still the same douchebag but merely become functional and kept himself in check (and only didn't go back into trading stock because he had his license permanently revoked)? Bear in mind Leo Di Caprio's character, not the real figure. Rule of Cautious Editing applies there.
    • Did Naomi really love Jordan and only divorced him because she was fed up with his behavior? Or was she just a Gold Digger who ended things when she realized she wouldn't be able to live her life of luxury anymore? God knows she'd have good reason to divorce him given all his antics (showing up intoxicated at his own house in full sight of his daughter, him delaying their arrival at her aunt's funeral to do his own business, endangering her life by going out into a storm, getting arrested by the FBI). But to increase the ambiguity of her character is the fact that she (grudgingly) stuck by him all that time and only left him when his fortune withered up.
    • Does Patrick Denham target corrupt Wall Street brokers because he's that noble? Or is he bitter over failing to get his broker license and taking out his resentment and jealousy out on them? Or is it a bit of both?
      • Denham's subway scene at the end is very open to interpretation. On one hand, he could be looking at the wretched people around him in pride, knowing that he protected them from someone like Belfort. On the other, he could be looking at them in regret, knowing that he could have taken Belfort's bribe and been somewhere better right now. Or, it could also be regret that even though he brought Belfort down, it didn't do anything to improve the lives of the others in the train car.
    • The small character of Kimmie's first appearance in the movie is her conning people into investing into penny stocks. As inspiring as Jordan's speech is in saying that Kimmie is a Rags to Riches story, she also is a part of this world of utter depravity and has swindled people out of money. How much sympathy does she really deserve?
  • Award Snub:
    • Five Oscar nominations (Best Picture, Best Actor, Best Supporting Actor, Best Director and Best Adapted Screenplay) and not a single win (though the winners were all very deserving), continuing Scorsese's unfortunate habit of having his best films released in years with incredibly competitive Academy Award seasons (The Departed aside). Some also felt that Margot Robbie deserved a Best Supporting Actress nomination, and that the film's editing and cinematography should also have gotten a look-in.
    • Some were a little more unsatisfied that Leonardo DiCaprio lost the Oscar for Best Actor to Matthew McConaughey, to the point that Honest Trailers made light of it a few times in their video on the film. When he finally won an Oscar for The Revenant, many viewed it as a Consolation Award for Wolf of Wall Street and his other performances.
  • Awesome Music: A staple for Scorsese's films but the use of 7horse's Meth Lab Zoso Sticker, a single released by a two man indie group is for some an incredible track which got a Colbert Bump thanks to the film.
  • Best Known for the Fanservice: Doesn't exactly apply to the film itself (though it is known for having copious amounts of nudity and sex), but this movie is the reason why Margot Robbie is recognized as a Ms. Fanservice in the media.
  • Broken Base: There's an ongoing debate as to whether this film glamorizes the villains or not. On the one hand, the characters are ultimately punished for their misdeeds and the final scenes demonstrate how unfair it is that Jordan goes to a luxury prison while Denham is stuck in his middle class lifestyle despite all the good he's done. On the other hand, the film focuses a lot on how the characters get to live large with their wealth and never shows how their actions impacted their victims and the ending can easily be interpreted as how their crimes ultimately pay as the punishment is a slap on the wrist.
  • Catharsis Factor: Given how long Jordan stays at the top while acting like an obnoxious and loathsome shit, finally seeing him lose is quite satisfying. This can also apply to his many other misfortunes throughout as well. His last defeat is however undercut by seeing him in a nice, fancy prison and knowing he'll still be able to influence others to become Slimeballs like him.
  • Crazy Is Cool: Mark Hanna. He defines himself as a racketeer who runs on masturbation and cocaine, and then on top of it, he's played by Matthew McConaughey. Then he predictably fails on Black Monday.
  • Crosses the Line Twice: SO many times. The movie chronicles a bunch of sleazy scumbags whose over the top shenanigans and juvenile hijinks are something to behold:
    • One example would be when Jordan and his boys see Naomi for the first time, and one guy says "I'd fuck her if she was my sister", and another says he'd let her give him AIDS.
    • Another memorable example being Donnie's explanation to what he'd do if he had a mentally-impaired child as a result of sleeping with his cousin.
    • Jordan dry humping the stewardesses like a madman while his friends and other passengers try to stop him. He gets restrained and passes out.
      Jordan: "I called the captain the n-word?"
      Donnie: "Yes. He was very upset."
  • Do Not Do This Cool Thing:
    • The movie has become to Crypto currency traders what Gordon Gekko is to Wall Street traders.
    • Business Insider offers supporting evidence. Likewise, Christina McDowell, daughter of one of Belfort's business associates, accused the filmmakers of glamorizing his crimes and likely inspiring others to do the same, though Belfort himself dismissed her allegations and questioned her credibility.
    • Martin Scorsese, for his part, has in the past criticized the idea of movies telling what the audiences to think and feel, believing that Viewers Are Geniuses and can sort out their moral compass for themselves and that this movie is "not made for 14 year olds."
  • Draco in Leather Pants: The number of viewers who actually like Jordan is rather unsettling given he's a shameless Villain Protagonist motivated only by a need for wealth and power, which he exploits in ways that are both dangerous and cruel.
  • Ensemble Dark Horse:
    • Matthew McConaughey as Mark Hanna who in the words of one critic tuned the movie like a concert conductor.
    • Jon Bernthal as Brad Bodnick. It helps that he's seemingly the only criminal in the film who isn't a hopelessly arrogant, hedonistic moron.
    • Aya Cash as Jordan's assistant Janet makes a strong impression with just a couple of brief appearances.
  • Evil Is Cool: Jordan Belfort is a whoring, parasitic cokehead but he's dressed in Armani, drives a Ferrari and is pretty cool. He flat out admits that his invitation to Denham to come to his yacht was his attempt to play a Bond Villain, complete with Bond Villain Stupidity. Plus he's played by Leonardo DiCaprio.
  • Germans Love David Hasselhoff: The film was really successful in several European countries.
  • Harsher in Hindsight: In July 2019, co-producer Riza Aziz was arrested for money laundering in Malaysia, lending some unfortunate Reality Subtext to this film.
  • He Really Can Act:
    • He had a solid reputation but Jonah Hill's performance here was seen by many as way beyond what people expected of him, with some comparing him to Joe Pesci, being a similar role of a sociopathic sidekick.
    • He's built a solid reputation since Titanic (1997), but for many people DiCaprio's performance here was the first one that made skeptics (who doubted his position as the successor of Robert De Niro in Scorsese's films) impressed, a role which transforms the romantic dreamboat into an unrepentant Large Ham vulgar sleazebag who people say is even worse than the crooks in Scorsese's gangster films.
    • Margot Robbie seriously impressed a lot of people in her first major role to the point that some felt she should have been nominated at the Oscars too.
  • Jerkass Woobie: Naomi, depending on who you ask. She becomes more sympathetic as she becomes subject to Jordan’s cheating and downright abuse as the movie goes on.
  • Magnificent Bastard: Brad Bodnick stands out in a film full of obnoxious, arrogant stockbrokers in over their heads as a calm, businesslike drug dealer who comes out looking the best. Already the "quaalude king of Bayside" with his profitable drug slinging operation, Brad proves his wits even further when he figures out Jordan's "sell me this pen" pitch by breaking it down to the simplest terms of "supply and demand." Concocting the scheme to use his Chantalle's family as money mules to smuggle Jordan's fortune into Switzerland, Brad is only caught when the unbearable Donnie mocks him into a fight in public. Even when imprisoned, Brad refuses to rat out Jordan or Donnie, and upon his release gracefully ends his association with Jordan's enterprise. Though he suffers a fatal heart attack mere years later, Brad avoids the humiliating downfall of Jordan and his associates, exiting the story happy and content with his lot.
  • Mexicans Love Speedy Gonzales: More often than not, brokers (in particular stockbrokers), financiers and bankers will say that they enjoyed this movie despite the film largely portraying people who work such jobs as greedy hedonists.
  • Memetic Mutation:
  • Misaimed Fandom:
    • One writer for Business Insider went to see the film with actual Wall Street people, and was disturbed by their enthusiastic reaction to Belfort and his cronies' wrongdoing.
    • Many critics have cited Jordan Belfont as being the Spiritual Successor to Gordon Gekko, who also inspired this.
    • There's also a small group that believe the film glorifies the Corrupt Corporate Executive or that Belfort escaped any consequences. One wonders if they even watched the film.
    • Like Glengarry Glen Ross before it, the film also became somewhat memetic among salesmen through means of Do Not Do This Cool Thing. It doesn't matter that the protagonist is shown as being incredibly immoral, hedonistic and egocentric — if you're a ruthless and silver-tongued salesman who'll play the mind games and do anything to close, then you too could be a ruthless, self-made multi-millionaire like Jordan and the film's finale more or less gives a Shrug of God, with the staging focusing on the audience of eager investors coming to Belfort's seminars despite serving time in prison and despite being exposed.
  • Moral Event Horizon: Jordan beating Naomi and attempting to kidnap their daughter after she tells him she's leaving him and taking full custody of the kids; his Villainous BSoD after it fails seems to indicate he sees it this way too. Though that's only if he hasn't crossed it in some people's minds already by disregarding Aunt Emma's death as more of the loss of $20 million and proceeding to deal with her funds rather than prepare her funeral. Hell, it can be said he crossed it long before that just by happily screwing so many people out of their money.
  • Nightmare Fuel: Jordan, in a cocaine-fueled rage, beats up Naomi and takes Skyler from the house in an attempt to run away with her and almost kill the both of them in a crash. Unlike almost every other sequence in the film, this one is completely Played for Drama and is especially gut-wrenching for anyone who has suffered from domestic abuse and seen their family life torn into pieces.
  • Older Than They Think: The moniker, "the Wolf of Wall Street", has actually existed as far back as the 1920s (maybe even further). There was even a 1929 film with the exact same title (Coincidentally also produced by Paramount). The moniker continued to be heard sporadically in popular culture over the decades between both films (for instance, the first ever Mr. Peabody & Sherman cartoon in 1959 has Peabody referring to himself as such).
  • One-Scene Wonder:
  • Retroactive Recognition: Aya Cash has a small role as Jordan's bossy secretary. A year later, she'd be much more recognizable for her lead role in You're the Worst and later The Boys.
  • Spiritual Successor:
    • Screenwriter Terence Winter and Martin Scorsese have essentially noted that this film does for White Collar crime what Goodfellas and Casino does for organized crime. Indeed, in Scorsese on Scorsese, the director predicted that there would be a film on white collar crime about fifteen years after Casino (he was off by three years):
      It's an interesting dilemma for Sam and Nicky. They both buy into a situation and both overstep the line so badly that the destroy everything for everybody. And eventually a whole new city comes rising out of the ashes of what they've destroyed. Who knows the reality of Las Vegas now, where you've gone from a Nicky Santoro to Michael Milken or a Donald Trump? Who knows where the money's going? But I'm sure it's got to be worth it, somehow, for those entrepreneurs to come in with the money. You'll probably see a film in fifteen years exposing what they're doing now.
      Scorsese on Scorsese Page 202-203, 1996 Edition.
    • The film has also drawn comparisons to Catch Me If You Can. Both works follow a charming white-collar criminal played by DiCaprio and who comes from humble beginnings to eventually live affluently off ill-gotten gains for a while.
    • The protagonist commits audacious crimes, goes to prison but finds that rather than punishment, he's found infamy and respect and is a sought after speaker with a book deal and movie. Is this Jordan Belfort or Rupert Pupkin from The King of Comedy? The final scene of Belfort giving a speech to the audience echoes the end of that film.
  • Signature Scene: The Once More, with Clarity take of Jordan's massive Quaalude trip where he, among other things, flops down a flight of stairs and opens the door of his Cool Car with his foot.
  • Too Bleak, Stopped Caring: Some viewers just can't get into the film on account of nearly every single character of note being despicably unrepentant criminals who spend a significant part of the runtime smugly ripping off innocent people and indulging in hedonistic lifestyles that they happily acknowledge as being awful.
  • The Woobie:
    • Teresa, Jordan's first wife. She fully loved and supported him and he repaid her by constantly cheating on her then divorcing her for his mistress.
    • Jordan's father Max whose visibly heartbroken when he sees his son refuse to quit his illegal activities and evade legal punishment.

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