Characters / The Last Boy Scout

Joe Hallenbeck

Joseph Cornelius "Joe" Hallenbeck

"Everyone hates you. You're gonna lose. …Smile, you fuck."

Played By: Bruce Willis

• Abusive Parents: The first time we see him talking with Darien, the two get into a screaming match where he berates her and chucks a jug of ice cream out the window because she insulted him. He's shown to genuinely care about her, and he's shown to be trying to be a better father in the ending.
• The Alcoholic: A depressing example. Joe is frequently seen drinking, and mentions that he frequently gets blackout drunk.
• Anti-Hero: Unscrupulous with some Nominal 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'
• Arch-Enemy: To Milo.
• Badass Boast: "You touch me again and I'll kill ya."
• Badass Longcoat: He wears the standard well-worn PI waistcoat.
• Berserk Button: Drug usage really pisses him off, as Jimmy learns the hard way.
• Butt-Monkey: He gets beaten up a lot over the course of the film.
• Catchphrase: "And then some."
• 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.
• Fallen Hero: Joe used to be a national hero and a confident, ethical Secret Service agent. Thanks to Baynard ruining his career and his subsequent downward spiral, Joe is now a shiftless, cruel drunk barely scraping by. His character arc is fueled by him climbing his way back to being what he once was.
• Genius Bruiser: He's a talented detective and very physically capable, even capable of killing a man with a single punch.
• Good is Not Nice: Joe is an honorable man with a strong code of ethics. He's also a total asshole.
• 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: A hard-drinking, smoking, tough-as-nails PI.
• Hell-Bent for Leather: He wears a black jacket for the first half of the movie.
• Heroic Self-Deprecation: Hallenback is very self-loathing, and freely admits to being a total Jerkass.
• He's Back!: It's made more explicit in the original script, but a large part of Joe's character arc is shifting back to the man he was before his disgrace.
• Hidden Disdain Reveal: Inverted. It turns out he used to be a massive fan of Jimmy while he was still playing.
• 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.
• Hypocrite: When Jimmy defends his drug addiction as helping him get by, Joe declares he duets along just fine without them, in spite of being a hardcore alcoholic.
• Jerk with a Heart of Gold: He's a cynical, misogynistic, foul-mouthed, somewhat sleazy, unhinged alcoholic who still always does the right thing and has a strong moral doe.
• Knight in Sour Armor: Pessimistic to the point of flat-out nihilism, but he still tries to do the right thing. Lampshaded in the original script.
  Jimmy: Damn. I knew there was a hero lurking under that gruff exterior.
  Joe: Yeah, I'm a prince. Shut the fuck up.
• Papa Wolf: Milo kidnapping Darien sets Joe into an Unstoppable Rage.
• Perma-Stubble: Lampshaded, as multiple characters point out he really needs to shave.
• Politically Incorrect Hero: "What are you, a fag?"
• Pre-Insanity Reveal: Hallenbeck is an drunken, shiftless, mentally unstable wreck of a human being when he's introduced, making it come as a shock when it's revealed he used to be a confident Ward Cleaver-esque Secret Service agent who once saved the President's life.
• Private Detective: That's his job after being kicked out of Secret Service.
• Rap Is Crap: He certainly thinks so, and makes a few quips about his disdain for it here and there.
  Milo: You think you're so fucking cool, don't you? Well, just once, I would like to hear you scream. In pain.
  Joe: Play some rap music.
• Revolvers Are Just Better: Joe owns a collection of revolvers. His main sidearm is a Smith & Wesson Model 19 snub (the weapon of the Secret Service).
• 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: Deconstructed. It looks badass, but it's made clear that Joe's smoking is an addiction, and it can get to pathetic lengths; at one point, he tries to smoke a cigarette stub he found on the ground.
• Sociopathic Hero: He definitely has his moments, including threatening to shoot Mike so Sarah would admit to their affair.
• Taking the Bullet: He did this to save Jimmy Carter from an assassination.
• Took a Level in Jerkass: He's implied to have been a stand-up guy in the past until his firing and subsequent ruined reputation triggered a downward spiral.
• Used to Be a Sweet Kid: It's implied he used to be a nice guy in the past, before his downward spiral turned him into a cynical asshole.

Jimmy Dix

James Alexander "Jimmy" Dix

"I figure you gotta be the dumbest guy in the whole world, Joe. You're trying to save the guy who ruined your career, and avenge the guy who fucked your wife."

Played By: Damon Wayans

• Bond One-Liner: "It's one of those new plastic keys. The kind that shred."
  Joe: The kind that shreds?
  Jimmy: Short notice. It was the best I could do.
  Joe: You did good, kid.
  Jimmy: I learned from the best.
• Broken Ace: He was once a star football player but ruined it with his various addictions.
• Broken Pedestal: To Joe, after he finds out about Jimmy's drug addiction. It quickly becomes a Rebuilt Pedestal.
• Butt-Monkey: Jimmy goes through a lot of suffering over the course of the film.
• Chronic Hero Syndrome: It's emphasized more in the original script, but Jimmy has a tendency to jump into trouble the second someone's in danger.
• Deadpan Snarker: He can deliver very witty lines like Joe.
• Freudian Excuse: Most of Jimmy's problems, including his drug addiction, can be traced back to his family being killed in a car accident while he was playing the best game of his life. He also notes that Marcone's incessant pushing of his players to physical extremes broke him.
• Friend to All Children: Despite his drug problems and short temper, he's remarkably good with kids, if Darian is any indication because they quickly bond with each other after a little friction.
• Good is Not Nice: Not as much as Joe, but he's still firmly on the side of good even if he's kind of a prick.
• Hollywood Atheist: During a self-pitying rant, he admits that he no longer believes in God after the death of his family.
• Iconic Outfit: His signature hat. Darien only recognizes him with it on.
• It's All My Fault: He blames himself for Cory's death after figuring out she only blackmailed Marcone because she was trying to get his job back.
• Jerk with a Heart of Gold: Downplayed, at least in comparison to everyone else. He's rough around the edges and has spiraled into addiction and hedonism, but he's shown to be a genuinely good guy who's a Friend to All Children.
• Made of Iron: He's still able to make a perfect throw even with a bullet in his hand.
• Vitriolic Best Buds: With Joe.

Sarah Hallenbeck

Sarah Hallenbeck

"You were never around. You know what? Fuck you, Joe. I was lonely!"

Played By: Chelsea Field

• Jerkass: She refuses to take responsibility for her affair and shifts the blame to Joe repeatedly.
• Jerkass Has a Point: While a lot of it is to deflect from her affair, she's entirely right in her criticisms of Joe.
• Jerk with a Heart of Gold: Ultimately, she still feels guilty for it and apologizes.

Darian Hallenbeck

Darien Hallenbeck

Played By: Danielle Harris

• Badass Adorable: She's a rather cute teenager, yet literally saved her father and Jimmy by pretending to be a lost girl and handing her father a .357 hidden in her teddy bear.
• Bratty Teenage Daughter: Oh, so very much, like angrily cussing at her dad and whatnot. Though it's pretty understandable, since the only person she acts like that towards is Joe.
• Break the Cutie: She is shown to be very traumatized after experiencing being kidnapped by Milo. She is also adorable.
• Cloudcuckoolander: She shows some signs of this, lie communicating to Joe through a puppet and believing in "Satan Claus".
• Deadpan Snarker: She's a total wiseass like her father.
• Freudian Excuse: She may be a foul-mouthed brat, but with a father like Joe, can you really blame her?
• From the Mouths of Babes: She says this to Marcone:
  Darian: Eat shit, you fucking redneck!
• Jerkass to One: Generally, she only acts like a jerk to Joe. Otherwise, she's rather friendly, and gets along swimmingly with Jimmy.
• Jerk with a Heart of Gold: She is foul-mouthed and rude but her heart is in the right place.
• Little Miss Badass: She rescues her dad by pretending to be a lost little girl and approaching a gang of cutthroat corporate mercenaries and hands her father a .357 hidden in her cat puppet.
• Little Miss Snarker: A teenage girl who is as wisecracking like her father.
• Miss Swears-A-Lot: She is shown to curse frequently around her father and did it once to Marcone.
  Darian: Eat shit, you fucking redneck!
• Used to Be a Sweet Kid: Flashbacks show that she used to be an adorable Cheerful Child who idolized her father. It's implied she Took a Level in Jerkass because of Joe's downward spiral.

Shelly Marcone

Sheldon "Shelly" Marcone

"That's what you never understood, Jimmy. Life is pain."

Played By: Noble Willingham

• Bad Boss: Marcone pushes his players to impossible physical extremes for the sake of a good game, and it's implied he encourages or at least allows them to turn to drugs to keep them going. By the time of the film, he has Milo threaten players with death for the sake of his burgeoning gambling ring. He flat-out admits he pushes them to such extremes because "life is pain".
• Big Bad: Marcone's scheme to legalize gambling and the lengths he'll go to to get it are what drive the plot.
• Dirty Old Man: He frequently solicits prostitutes by his own admission, and fondly reminisces about having sex with Cory.
• Evil vs. Evil: Senator Baynard is undoubtedly a horrible person, but Marcone is no better.
• Evil Old Folks: Marcone is both old and very evil.
• Fat, Sweaty Southerner in a White Suit: Well, he isn't fat, but otherwise fits the bill.
• Faux Affably Evil: He acts like a polite Southern gentleman and speaks casually with Joe and Jimmy, but it doesn't take long for him to show what a vile bastard he really is.
• Greed: His main motivation and flaws. He plans to legalize sports gambling and when Senator Banyard demands $6 millions in order to make the plan work he decides that killing him is gonna be "cheaper."
• Hoist by His Own Petard: He steals the wrong suitcase containing the bribe money, and instead gets the suitcase bomb that was meant for the Senator.
• Karmic Death: He steals the suitcase bomb from Joe's car, thinking it's the bribe money, and is blown up when he opens it. Lampshaded by Joe and Jimmy, who chuckle over the irony.
• Kick the Dog: He shoots Jimmy in the hand for not "being able to take the pain".
• Light Is Not Good: He dresses primarily in white clothes, and is an evil bastard.
• Smug Snake: He's nowhere near as smart as he thinks he is.
• The Sociopath: He's a greedy and overly evil man hidden under a politely façade who is willing to have anyone killed in order to achieve his objectives with no remorse at all.
• Straw Nihilist: He declares to Jimmy that "Life is pain", and shoots him in the hand to prove his point.

Milo

Milo

"I am the bad guy."

Played By: Taylor Negron

• Adaptational Nice Guy: While Milo's a piece of work in the film itself, in the original screenplay he's much worse, running a snuff film operation to get his sadistic jollies.
• Arch-Enemy: To Joe.
• Ax-Crazy: He's gleefully murderous, and at one point threatens to cut Joe's eye out for insulting him.
• Blue Is Calm: Subverted. Milo has a blue Color Motif and wears primarily blue clothing, and he's almost always perfectly serene and composed. It gradually becomes clear that he's just barely restraining the snarling maniac he really is.
• Boom, Headshot!: His signature move is this. He kills McCaskey and the pool owner with a bulletin to the head, and tries to do the same to Baynard.
• Card-Carrying Villain:
  Joe: You're the bad guy.
  Milo: I am the bad guy.
• Cold Sniper: Played with. In the climax, he uses a sniper rifle for Baynard's assassination, but by this point he's dropped his earlier composed demeanor due to a Villainous Breakdown.
• Cop Killer: He kills McCaskey and later guns down a SWAT officer during the climax.
• Creepy Monotone: Courtesy of Taylor Negron.
• Creepy Blue Eyes: His blue eyes are only used to accentuate what a merciless killer he is.
• Cruel and Unusual Death: Getting shot dozens of times and then ground into paste by a helicopter is clearly unpleasant.
• Disproportionate Retribution: He doesn't take Joe telling him to go fuck himself well.
  Milo: Okay. Now, that's not very polite. (Pulls out a switchblade and presses it to Joe's face) It's very abusive-sounding. What would you do, Joseph, if somebody told you to go fuck yourself? Would you cut one of their eyes out?
  Joe: No.
  Milo: No? What would you do?
• Dissonant Serenity: Milo almost always speaks in a calm, collected tone. If he isn't doing that, that means he's angry, which means you should run.
• The Dragon: He's Marcone's right-hand man.
  • Dragon-in-Chief: Though Marcone technically is the Big Bad of the film, Milo gets the most screentime.
• Face of an Angel, Mind of a Demon: He's a somewhat handsome, normal-looking man who's also a ruthless, sociopathic mercenary.
• Faux Affably Evil: He acts polite and affable, but quickly proves to be a sadistic maniac after Joe insults him one too many times.
• Freak Out: He completely loses it after the assassination attempt is foiled, trying to gun down Jimmy, Joe, and a police helicopter in a fit of rage.
• Hair-Trigger Temper: While he tries to keep it under wraps so his Faux Affably Evil act can work, it becomes clear very quickly that Milo has a nasty temper and a fondness for Disproportionate Retribution.
• Hate Sink: He's a smug, patronizing killer with a disregard for human life who murders people at the slightest (or sometimes no) provocation.
• Helicopter Blender: After being shot by a SWAT team, Milo tumbles off a catwalk and straight into the blades of a helicopter.
• Jerkass: Even when he's trying to put on a friendly act, he's too smarmy and patronizing to make it work.
• Kick the Dog: He loves doing this. Killing a random civilian, taking Darien hostage, gunning down McCaskey just to frame Joe, and plenty more.
• Light Is Not Good: Milo dresses in light clothing and has dirty blonde hair, and he's shown to be a ruthless, even sadistic killer.
• Made of Iron: He survives crashing into the pool with nary a scratch.
• Multiple Gunshot Death: He's riddled with bullets by a SWAT team, though it's the subsequent Helicopter Blender that kills him.
• Precision F-Strike: Whenever Joe really pisses him off, Milo starts dropping F-bombs like crazy. During his Villainous Breakdown, he loses it entirely and starts speaking in nothing but these.
• Psycho for Hire: He's a gleefully psychotic mercenary hired by Marcone who takes great pleasure in what he does.
• Rage Breaking Point: After enduring numerous set-backs, Milo snaps and goes into an animalistic rage after the assassination attempt is foiled.
• Sesquipedalian Loquaciousness: Milo uses a ton of fancy words, and insists on referring to everyone by their full names.
• Sinister Switchblade: He carries one, which he threatens to use to cut Joe's eye out and uses to stab him in the climax.
• Sir Swears-a-Lot: As Hallenbeck increasingly pisses him off, Milo starts swearing more and more until he's dropping the F-bomb on an hourly basis.
• Smug Snake: Milo is almost perpetually calm and smarmy, making it pretty satisfying when Joe starts getting under his skin.
• Soft-Spoken Sadist: Milo always speaking in a Creepy Monotone, even when he's threatening people. In fact, especially when he's threatening people.
• The Sociopath: A textbook example in film. He's superficially charming, but has no regard for human life and takes glee in his killings.
• Villainous Breakdown: Towards the end of the film, Milo becomes increasingly angry as Joe and Jimmy repeatedly get in his way. It culminates in a full-blown meltdown when his attempt on Baynard's life is foiled.
• Villainous Valor: One thing Milo does not lack is bravery. He's always in the action and never backs down, even firing at a police helicopter when the officers aboard try to arrest him.
• Would Hurt a Child: He kidnaps Darian and it's implied that he would have harmed her if Joe didn't back off.
  Milo: You back off Joseph or I'm gonna show your daughter what a hot date I am!

Cory

Cory

Played By: Halle Berry

• 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: Halle Berry in a Stripperiffic outfit.
• We Hardly Knew Ye: Only around for a few scenes before being gunned down.

Senator Calvin Baynard

Senator Calvin Baynard

Played By: Chelcie Ross

• Blackmail Backfire: A thoroughly unsympathetic example. Marcone was going to bribe him, but the Senator does not likes the amount originally offered and not only makes clear to Marcone that his price is $6 million, he tries to blackmail Marcone info handing it over. For the insult and because it would be cheaper, Marcone decides to kill him.
• Bribe Backfire: When Marcone tries to bribe him to legalize gambling, he makes clear to Marcone that he will take no less than $6 million as bribe. Marcone decides that killing the Senator is the cheaper option.
• Corrupt Politician: He's so corrupt that when Marcone bribed him, he tried to blackmail him into giving him more money.
• Greater-Scope Villain: He's the one who got Hallenbeck fired and triggered his downward spiral, and he clearly is up to some sort of shady business, but the main threat is Marcone's efforts to kill him for the sake of his own evil plan.
• Hate Sink: A corrupt and greedy senator and as we find out a women abuser in the meantime. Also the main responsible for Joe's downhill. Some even wish that Joe won't save him from the assassination attempt.
• Sleazy Politician: Baynard is a smug, corrupt bastard with an obvious fake smile constantly plastered on his face.
• Spared by the Adaptation: He died in the original script.
• Ungrateful Bastard: After Hallenbeck saved him, Baynard angrily demands to have him arrested. Hallenbeck replies by punching him in the face and gut.
• Would Hit a Girl: He's seen violently abusing his one-night-stand in a flashback. Joe punched him in the face for this.

Lieutenant Benjamin Bessalo

Lietenant Benjamin Bessalo

Played By: Joe Santos

"I could nail you for obstruction."

• Inspector Javert: He's convinced that Hallenbeck is some kind of a criminal even before he starts stumbling onto evidence.
• Irrational Hatred: It's unclear why he hates Joe so much, but he really does.
• Jerkass: Though only when he's dealing with Joe and Jimmy, who aren't the nicest guys themselves. He's pretty polite with Sarah and McCaskey.
• Wrong Genre Savvy: He seems to think he's in an old-school cop show, and Joe is the Villain of the Week who's Obfuscating Stupidity to avoid conviction.

Mike Matthews

Michael "Mike" Matthews

"How long we been friends, Joe?"

Played By: Bruce McGill

• Alliterative Name: Mike Matthews.
• 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.

Lieutenant Mick McCaskey

Lieutenant Mick McCaskey

Played By: Clarence Felder

• Boom, Headshot!: Milo shoots him in the face.
• Death by Adaptation: He survived in the original script.
• Foil: To his partner Bessalo. They both suspect Joe of being a criminal, but McCaskey is far less agressive and more level-headed in his approach.
• Nice Guy: The nicest character in the film. While everyone else is a Jerkass in some way or another, McCaskey is nothing but polite and cordial.
• Sympathetic Inspector Antagonist: Unlike Bessalo, McCaskey is a kindhearted, respectful man who tends to follow his partner's lead.
• Too Good for This Sinful Earth: The sole Nice Guy in a film full of assholes gets killed by Milo for being at the wrong place at the wrong time.

Billy Cole

Billy Cole

"Ain't life a bitch?"

Played By: Billy Blanks

• Driven to Suicide: He blows his brains out after gunning down several members of the opposing team in public, which was captured on national television, out of his fear of being killed by Milo.
• Profane Last Words: "Ain't life a bitch?"
• Small Role, Big Impact: He dies in the opening scene, but his death shows how ruthless Marcone and Milo are and hints at their Evil Plan to legalize sports gambling.
• Unnecessary Roughness: Brings a Beretta to a football match and blows away several opposing players. Played for tragedy because he brought it to kill himself and in retrospective it's evidence of how absurdly vile the bad guys are.
• We Hardly Knew Ye: He's only around for the opening scene before killing himself.

Chet

Chet

"Hey baby, I thought you were tough!"

Played By: Kim Coates

• Bullying a Dragon: He punches Joe twice despite his threats and mocks him afterwards. This costs him his nose...and his life.
• Cruel and Unusual Death: Joe punches his nose straight into his brain.
• Hate Sink: He's an unwarrantedly smug, annoying thug who acts like an immature douche. By the time Joe kills him, it's a relief.
• Jerkass: He's smug and annoying, to a highly obnoxious degree.
• Large Ham: Kim Coates really dials up the obnoxiousness for his performance.
• Psychopathic Manchild: He acts like a cruel and bratty kid playing pranks.
• Smug Snake: He smugly mocks both Joe and Jimmy when he has them at his mercy.
• Underestimating Badassery: He gleefully dismisses Joe as a pathetic drunk and smacks him around while believing he can't fight back. Turns out he was dead wrong.
• Verbal Tic: He says baby a lot, generally when he's excited.

Pablo

Pablo

"Milo warned us to watch out for this guy."

Played By: Frank Collison

• Beard of Evil: A villainous thug with a beard.
• Dropped a Bridge on Him: He's abruptly killed when he's blasted by a shotgun. It's in quick cuts, so it's hard to even tell he died.
• Mauve Shirt: A villainous example. He doesn't get as much personality as the other villains, but he still shows up the most outside of Milo and Marcone.
• Oh, Crap!: He freaks out after Joe kills Chet.

Alley Thug

Alley Thug

"Oh, you're real cool for a guy about to get a bullet."

Played By: Badja Djola

• Affably Evil: He's surprisingly friendly with Joe while trying to kill him, admitting that it's Nothing Personal and laughing at his jokes and insults.
• No Name Given: Outside of Joe's nicknames, nothing.
• Punch-Clock Villain: Admits killing Joe is Nothing Personal.
• Scary Black Man: He's very imposing and very intimidating.
• Slashed Throat: Joe slices his throat open with a bottle.

Big Ray Walton

Big Ray Walton

Played By: Tony Longo

• Asshole Victim: Jimmy breaks his nose, and later threatens him with a shotgun, but Ray's such a dick that it's hard to care.
• Jerkass: He's an abrasive prick who nearly drowns a woman because she wouldn't give him a blowjob.