- Where Jordan's first wife finds him having sex with Naomi and is in hysterics.
- Jordan narrating on how Brad passed away of a heart attack 2 years after being released from prison at the young age of 35. You know its serious when Jordan uncharacteristically sounds saddened and mournful, in contrast to ignorant he is of other people like Emma dying.
- The fact that we dont see him pass away actually makes the scene sadder. What we see is Brad happily enjoying the company of women and his friends, all while Jordan is narrating his passing. Brad doesnt know that his happiness would eventually die out after 2 years.
- When Denham is riding the dinky subway while Jordan is in "prison" playing tennis. It sells the idea that Jordan said earlier: being good sucks. It's depressing because who is the real winner here?
- Mad Max's despair when Jordan doesn't Know When to Fold 'Em. You can tell that he genuinely wanted things to go the way they should have, as he desperately pleads and the chanting drowns him out.
- The darkly comical scene where Naomi announces her intention of divorcing Jordan. It's rather heart-wrenching (and slightly terrifying) to see Jordan, in a cocaine-fueled rage, take Skyler from the house in an attempt to run away with her and almost kill the both of them in a crash. What makes the scene sad is Jordan's frustration at seeing he is losing everything and, knowing he can't do anything about it, trying to keep the one part of his life he feels is dear to him.
- And given Jordan's status as a Villain Protagonist, you can't help but root for Naomi in this scene. Letting her husband have one last fuck despite obviously hating it, getting socked in the face and screamed at when she says she wants a divorce, and almost having her daughter kidnapped, she goes through a lot in about five minutes. Made worse by the fact that, while you can interpret her marriage to Jordan as gold-digging or genuine, she consistently has care and concern for her daughter. Jordan almost took the one person we see her caring about.
- When Denham shows up to arrest Jordan after his note to keep Donnie from incriminating himself is found. Yeah, at this point of the film it might be hard to feel any sympathy for Jordan. However it's still sad that the one halfway decent and selfless thing he tried to do backfired so quickly. Even worse is that Donnie ratted him out.
Tear Jerker / The Wolf of Wall Street