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- Anti-Hero: Type III with some Type V moments. Aside from being a self loathing, pessimistic, chain smoking, borderline misogynistic bastard ("...and then some."), he also gives a sinister death threat to two of the badguys. He doesn't lie, something the badguys learnt the hard way. Still, compared to the people he's fighting, he's 'The Last Boy Scout'
- Badass Boast: "You touch me again and I'll kill ya."
- Deadpan Snarker: Easily the snarkiest in the entire film.
- Embarrassing Middle Name: After Jimmy tells him that "Danger is his middle name", Joe tells in turn that his middlename is Cornelius.Hallenbeck: You tell anybody, I'll kill you.
- Happy Dance: He tells Jimmy that if he survives their adventure, "I'm gonna dance a jig." After he defeats Milo, that's exactly what he does.
- Hardboiled Detective
- Heroic Self-Deprecation
- Honor Before Reason: Jimmy lampshades it by pointing out that he is currently risking his life and liberty to save a man who unjustly got him fired and to avenge the death of a man who was sleeping with his wife and most likely tried to get him killed.
- Jerk with a Heart of Gold
- Knight In Sour Armor
- Papa Wolf
- Politically Incorrect Hero: "What are you, a fag?"
- Screw the Rules, I'm Doing What's Right!: What got him kicked out of the Secret Service: He was standing guard outside senator Baynard's hotel room listening to a woman's screams as the senator was beating her up until he finally went inside and punched the senator's teeth in.
- Smoking Is Cool
- Card-Carrying Villain:Joe: You're the bad guy.Milo: I am the bad guy.
- Creepy Monotone: Courtesy of Taylor Negron.
- Dissonant Serenity
- The Dragon: He's Marcone's right-hand man.
- Faux Affably Evil
- Helicopter Blender: His fate.
- Psycho for Hire
- Sesquipedalian Loquaciousness
- Sir Swears-a-Lot
- Soft-Spoken Sadist
- The Sociopath: A textbook example in film.
- Villainous Breakdown: Towards the end of the film, Milo becomes considerably less calm and collected.
- Disposable Woman: She gets cut down by machine-gun fire in the first third of the film. While Jimmy teams up with Joe to solve her murder, he never seems all that broken up about her death and the snarky, bantering tone of the rest of the film seems incongruous at best in that light.
- Ms. Fanservice
- Stuffed in the Fridge: An especially egregious example when you consider that Joe and Jimmy spend the rest of the movie tossing out flippant one-liners.
- We Hardly Knew Ye
Senator Calvin Baynard
Lieutenant Benjamin Bessalo
- Alliterative Name
- Asshole Victim: Considering he slept with Sarah and probably set up Joe to get killed, nobody particularly mourns after he's blown up. Jimmy even calls him "a scumbag private detective" at one point.
- Jerkass: Very obnoxious.
- Slimeball: His attempts at being charming fall flat. One wonders what Sarah and Joe saw in him.
- With Friends Like These...: Why Joe stuck around with him for so long remains a mystery.