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Played By: Johnny Depp
- Affably Evil: Dillinger is handsome, charming, and won't hesitate to smash your face against a hard surface if you stand between him and something he wants, like Billie Frechette.
- All Girls Want Bad Boys
- Badass Longcoat: And how. They're good for concealing Thompson submachine guns.
- Foregone Conclusion: Dillinger's eventual death at the end.
- Historical Beauty Update: Hardly surprising, seeing as he's played by Johnny Depp.
- Impersonating an Officer: Does this quite memorably near the end of the movie; he even asks for the score on a baseball game that is going on!
- Manly Tears: When he watches the woman he loves being arrested and put into handcuffs because of her association with him.
- The Danza
- Trojan Prisoner: We open with this.
- Villain Protagonist: Subverted in that even the public considered him more of an Anti-Hero than a villain.
- We'll See About That: Dillinger says this to Purvis after being taunted that he'll never leave his jail cell until being removed for his execution in the electric chair. Though Purvis and Dillinger never actually spoke to each other, Dillinger did have multiple in-prison encounters with his original pursuer - Indiana State Police detective Matt Leach, who was somewhat more competent than the FBI in pursuing Dillinger.
- You Must Be Cold: Dillinger does this twice: once to a hostage bank teller and once to Billie. Both times, he hands these girls coats. All of it is Truth in Television as this was considered one of Dillinger's more renowned trademarks.
Played By: Christian Bale
- Hero Antagonist
- He Who Fights Monsters: His entire arc. You can clearly see in Bale's performance each time he compromises his values for the sake of getting the job done, and how much it weighs on him. Even Dillinger comments on this
- Idiot Ball: Tends to take it and run with it when it concerns Dillinger
- Police Brutality: While he himself does not participate, he is well aware of how several members of his squad got their information - but he draws the line at slapping around a woman.
- The case in question, Billie Frechette, might be because Purvis knows that she is an innocent person who probably knows little of what Dillinger was up to. In real life, his secretary also was appalled at the way Billie Frechette's interrogation went.
- Slowly Slipping Into Evil: Arguably passed this when he allowed the torture of Tommy Carroll