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Played By: Nicolas Cage
- Apple of Discord: Attempts this when asking why a militant black man like Diamond Dog is taking orders from a skinhead white guy. It fails when Diamond Dog explicitly says he's The Starscream.
- Badass: Best example is probably when he takes a bullet in the arm and doesn't even blink.
- Big Damn HeroesWhat do you think I'm gonna do? I'm gonna save the fuckin' day.
- Chronic Hero Syndrome: Can't get himself to leave Baby-O or the remaining guards to die.
- Crime of Self-Defense: He's attacked by three guys who try to make a move on his wife. He kills one of them when they pull a knife on him. The others flee, taking the knife, thus hiding the evidence that he used necessary force. As a result, the judge gives him 7-10 years, of which he serves 8.
- Dark and Troubled Past: Implied he had one and he joined the army to straighten himself out.
- Honor Before Reason: He's questioned by several people as to why he didn't get off the plane when he had the chance. He simply refused to leave diabetic Baby-O behind with no insulin.
- Major Injury Underreaction: Gets shot in the arm without even flinching.
- Messy Hair: Poe meant to get a haircut that day.
- No One Gets Left Behind: He won't leave the plane when he has the chance because he's afraid of what will happen to Baby-O and Bishop.
- Not So Different: Cameron and Cyrus are both prisoners, each with a Dark and Troubled Past, and both are praised for bettering themselves (Larkin notes that Cyrus earned a doctorate, and Tricia praises Cameron for joining the Army ). Both are also notably opposed to the rapist Johnny 23, and they seem to share the same wry sense of humour, which endears Cameron to Cyrus for a while. However, Cameron got sent to prison for one manslaughter, while Cyrus killed multiple inmates while inside said prison.
- Papa Bear"You ain't gettin' near my daughter. Buckle up!"
- Punctuated! For! Emphasis!:YOU! DON'T! TREAT! WOMEN! LIKE! THAT!!!
- Sleeves Are for Wimps: Poe ditches his prison shirt in favour of a sleeveless skivvy halfway through the movie, and never changes out of it.
- What Have I Done: Had this after killing Billy Bedlam.
- Wife-Basher Basher: He won't tolerate violence against women, which is what gets him locked up in the first place. He also beats the shit out of Johnny 23 for attempting to rape Bishop.
Mike “Baby-O” O’Dell
Played By: Mykelti Williamson
- Badass: He's shown in the beginning saving Cameron from a fire during a riot, burning his arm in the process.
- Black Best Friend: He meets Poe in prison early into Poe's sentence and they are inseparable since.
- Determinator: Tries to rescue Bishop from Johnny 23 while in the late stages of dying from lack of insulin.
- Ill Guy: He's diabetic, and a scene has Poe going after insulin.
- Hypocrite: Admits later on that he doesn't believe in God.
Cyrus the Virus
Cyrus “The Virus” Grissom
Played By: John Malkovich
- And Your Little Dog, Too!: Threatens to kill Casey Poe.
- Ax-Crazy: This guy is an absolute maniac willing to slaughter everyone around him at any given moment. In all, he's responsible for almost 30 deaths in the film, most of them prison guards or National Guard members.
- Badass: With emphasis on BAD, but he's still pretty awesome.
- Bald of Evil: He's a maniacal serial killer with no hair.
- Beard of Evil: Sports an evil looking goatee.
- Big Bad: His actions are the impetus for the film's plot. He put together the whole hijacking, looking to get away.
- The Chessmaster: Gives the orders on a plan he's clearly thought out well in advance. See The Evil Genius.
- Cruel and Unusual Death: He dies by being chained to the ladder of a speeding fire engine, hurled through a bridge and onto some electrical wires paralyzing him and finally getting his head crushed in a rock crusher.
- Crazy-Prepared: Somehow built a bomb in his cell in case his jailbreak plan is found.
- Death by Looking Up: Gets his head crushed by a pile driver.
- Even Evil Has Standards: Despises rapists.
- The Evil Genius: If Poe hadn't been on the plane, he likely would have gotten away with his plan flawlessly.
- Evil Is Hammy: John Malkovich is clearly having fun playing Cyrus.
- Horrible Judge of Character: Kept trusting Poe, until the boneyard escape.
- Omnicidal ManiacLarkin: Likes to brag that he's killed more men than cancer.
- Politically Incorrect Villain: He’s mildly racist, although he may have been using the N-word just to shake up Willie Sims when he takes Pinball hostage. He also told Baby-O too call the Affirmative Action Office when he complains.
- Rape Is a Special Kind of Evil: He hates rapists.
- Rasputinian Death: Gets stabbed in the foot, handcuffed to a fire truck's ladder, tossed off it, dropped on some electrical cables and finally has his head smashed in by a piledriver.
- Red Baron: "The Virus"
- Villainous Breakdown: He loses his composure first when Poe stabs him in the leg, then when he is cuffed just as the fire truck crashes.
Nathan Jones AKA “Diamond Dog”
Played By: Ving Rhames
- Character Death: Blown to pieces when Poe rams him with a police motorcycle.
- Horrifying the Horror: Seems genuinely scared when he's removing Garland Greene's restraints.
- Leeroy Jenkins: Was the first of the cons to escape and he tackles a bunch of cups by himself shouting "Allah u Akbar!"
- Malcolm Xerox: He's a black militant who hates whites. Poe even calls him out on it, wondering why he's taking orders from a white guy.
- Politically Incorrect Villain: Calls white folk "pig" and "hillbilly".
- Red Baron: "Diamond Dog"
Garland Greene AKA the "Marietta Mangler"
Played By: Steve Buscemi
- Affably Evil: He's one of the most dangerous men on the plane - but calm, snarky and seemingly harmless.
- Brick Joke: Unaccounted for after the ending plane crash. We don't see any of him until right before the credits... when he turns out to have made an absolute fortune gambling in Vegas.
- Chewing the Scenery: When he sings "He's Got The Whole World In His Hands" during the plane crash.
- Creepy Monotone: Most of his scenes.
- Deadpan Snarker: With quotes such as "Define irony. Bunch of idiots dancing on a plane to a song made famous by a band that died in a plane crash."
- Dissonant Serenity: A plane crash couldn't crack this man.
- The Dreaded: The most dangerous criminals in the country get trumped by a little man in white.
- Informed Attribute: Had supposedly killed more people than any convict on the plane, and had the absolute highest amount of security for transporting him. However, whilst he definitely alludes to having formerly killed people, we never really see any of his murderous aspects on-screen, to the point where it looks like he just might have been cured of them. It's still implied that he murdered one of the guards, and that doing so made him "feel better".
- Karma Houdini: Though all his villainy is in his backstory. During the movie Garland instinctively realizes Poe is a good guy pretending to be a hard con, and has a lengthy dialogue about ironic situations about how a good man has to act evil to survive. The fact that Garland intentionally leaves a little girl alive during the plane refueling hints that by the end of the movie Garland has decided to act good.
- Man in White: Wears a white prison uniform.
- Serial Killer: With a body count of 30.
- The Stoic: Even when the plane is crashing, he sings "He's Got The Whole World In His Hands" while other prisoners are panicking and shouting at him to shut up. He even seemed to enjoy it
- Wild Card: It's unclear what he's going to do at any given time, acting more like a ticking time bomb everyone is slightly wary of.
William "Billy Bedlam" Bedford
Played By: Nick Chinlund
- Ax-Crazy: He's not called "Billy Bedlam" for nothing. See Disproportionate Retribution
- Badass: He gives Poe a hard fight. If it wasn't for a bent-outward pipe, he would have smashed Poe's head in.
- Beard of Evil: Like Cyrus, he sports a goatee.
- Disc One Final Boss: Gets killed midway through the film despite being touted as one of the big bad trio, and replaced by Swamp Thing in the climax.
- Disproportionate Retribution: Our Billy caught his wife in bed with another man. He left them alone, but drove four towns over to his wife's family's house. He proceeded to kill her parents, her brothers, her sisters, and even her dog.
- Evil Laugh: He has an intimidating chuckle.
- Evil-Detecting Dog: He knew something wasn't right with Poe from the start.
- Famous Last Words: "Die, punk!"
- He Knows Too Much: Finds the info on Poe's status as a parolee in the cargo hold. A minute after that, he's dead.
- Impaled with Extreme Prejudice: During a fight with Poe in an enclosed space, he's pushed back onto bent-outward pipe.
Played By: MC Gainey
- Affably Evil: He seems like a fun guy except for the company he keeps. MC Gainey, who has a history of playing mostly villains, considers him a favourite.
- Beard of Evil: Again, due to being played by legendary beard-haver MC Gainey.
- Cruel and Unusual Death: Larkin floods the fire truck Swamp Thing drives. He smashes through the windshield and probably got run over.
- The Evil Genius: He's a pilot and knows how to bypass and remove the plane's transponders so that it can't be tracked.
- Iconic Outfit: His helmet.
- Mr. Fixit: Knows quite a bit about planes and how to keep them going.
- Only Known by Their Nickname: His real name is never given.
- Southern-Fried Genius: He's a Southern redneck, and also one of the most intelligent characters and certainly the most technically proficient.Pinball: What's up, man. So, you Swamp Thing?Swamp Thing: That's right.Pinball: Flyin' the plane?Swamp Thing: That's right.Pinball: It's amazing the shit you white trash know.Swamp Thing: [laughs] That's right!
Johnny Baca AKA “Johnny 23”
Played By: Danny Trejo
- An Arm and a Leg: Loses his tattoo arm, not to mention his life, in the plane crash.
- Cruel and Unusual Death: Dies (or so we must assume) when one or both of his handcuffed arms are torn from the rest of his body. Couldn't have happened to a nicer guy.
- Meaningful Name: So named because he was convicted of 23 counts of rape. He claimed to raped more than 23 women, though.
- Politically Incorrect Villain: He's a misogynist who refers to his victims as "marranitas" - which translates as "little piggies". In Latin America, a woman who enjoys sex, particularly degrading or hard sex, would be called this.
- Rape Is a Special Kind of EvilCyrus: "I despise rapists. For me, you're somewhere between a cockroach and that white stuff that accumulates at the corner of your mouth when you're really thirsty. But, in your case, I'll make an exception."
- Tattooed Crook: Courtesy of being played by Danny Trejo. Notably, Johnny states that 23 tattoos on his arm each represent the 23 women he raped.
- The Friend Nobody Likes: Both the good guy and the main bad guy hate this man. No one bats an eye when Poe cuffs him.
Joe "Pinball" Parker
Played By: Dave Chappelle
- Affably Evil: Pinball is a pretty fun guy and doesn't seem overly malicious.Pinball: Armed robber, arsonist, dope fiend. I'm a hell of a Nice Guy. I just got caught.Poe: Aw, shucks.
- Apologetic Attacker"If you get through this alright, hope you don't hold a grudge."
- Black Dude Dies First: Of the inmates directly involved in the takeover of the Jailbird, he's the first to die.
- Car Cushion: He falls from the plane onto a moving car.Diamond Dog: Bye, Pinball!
- Chekhov's Skill: His skills in arson was important in the hijacking.
- Deadpan Snarker: Well, he is a Dave Chappelle character.
- Distracted by the Sexy: He meets a cute girl while stashing the transponder and forgets to get back on the plane.
- Freudian Slip:"I work for the Department of Erec... Corrections."
- Karmic Death: He tries to get back on the plane. Unfortunately for him, the only guy who sees him is the guy he burnt earlier, who simply smiles as he gets caught in the plane's landing gear.
- Playing with Fire: Pinball is an arsonist.
- Reality Ensues: It's not a good idea to run alongside a plane.
Played By: Jesse Borrego
- Ain't Too Proud to Beg: Tries this on Cyrus when Larkin foils his escape attempt by wrecking his plane. Cyrus doesn't buy it and burns him.
- Blatant Lies: He desperately tries to bluff Cy about his attempted escape.Cindino: "We were coming... to get you."
- Chronic Backstabbing Disorder: From what Poe knows of Cindino's history, he guesses that the drug lord's probably not the best of allies. He was right.
- Killed Mid-Sentence:Cindino: "Cy-"Cyrus: "onara!" (Lights the gasoline from the plane)
- Man on Fire: An enraged and betrayed Cy sets him on fire.
- Screw This, I'm Outta Here!: Decides to leave the rest of the cons when things start to get hectic. Though he was planning to do so in the first place.
Ramon "Sally-Can't-Dance" Martinez
Played By: Renoly Santiago
- Bury Your Gays: Subverted. He is one of the few survivors. He was however the first to get re-arrested.
- Camp Gay: You don't really get more limp-wristed that him.
- Plucky Comic Relief: Of the Queer People Are Funny variety.
- Sissy Villain: To the point where Poe slaps him instead of punching him during a fight.
- The Smurfette Principle: The closest thing to the only female prisoner. He's referred to as "girl" and "sister" by other inmates and a cop calls him "lady" when he gets caught.note
- He even refers to men as a separate gender.
- Wholesome Crossdresser: Dons a lavender dress he finds right after the cons land at Lerner Airfield.
Guard Sally Bishop
Played By: Rachel Ticotin
Played By: Steve Eastin
- Deadpan Snarker: He fancies himself as this."The in-flight movie is I'll Never Make Love To A Woman On The Beach Again and it's preceded by the award-winning short No More Steak For Me, EVER."
US Marshal Vince Larkin
Played By: John Cusack
- Badass: Shining example has got to be when he saves the soldiers from the prisoners in a bulldozer.
- Deadpan Snarker: He's played by John Cusack, so this is a given. He's most snarky when Malloy fucks up.
- Description Porn: Describes Billy Bedlam, Diamond Dog and Cyrus the Virus but skimps when it comes to Poe.
- Deuteragonist: Plays this role to Poe's Protagonist.
- Mr. Exposition: He gives us the backstories of the Carnival of Killers who are onboard the plane.
- Reasonable Authority Figure: He doesn't want to shoot the plane down as there are innocents on board.
- Sesquipedalian Loquaciousness: Lampshaded. Malloy refers to him as "Dictionary Boy" to which he responds that "Thesaurus Boy" would be more appropriate.
- Strawman Political: An interesting case. He's every bit the liberal stereotype... except he's also the competent, on-point badass Deuteragonist.
DEA Agent Duncan Molloy
Played By: Colm Meaney
- Cool Car: His car is awesome. Larking borrows it to get to Lerner Airfield, where it gets destroyed.
- Inspector Javert: Considers all of the cons to be monsters.
- Jerk with a Heart of Gold: Molloy is aggressive, short-tempered, irritable and downright bloodthirsty, not to mention the level of vitriol he levels at Larkin. When it comes down to it, however, he does the right thing.
- Large Ham: He's pretty much constantly shouting, which suits his Hot-Blooded nature.
- Not Even Bothering with the Accent: Colm Meaney's heavy Dublin accent is fairly hard to conceal, to be fair.
- Officer O'Hara: It's never made clear if he's supposed to actually be Irish or just of Irish descent, though Colm Meaney's accent is difficult to cover up anyway.
- Pet the Dog: He cancels his order to shoot down the plane when he talks to Poe directly via radio and is told of his plight.
- Rabid Cop: He pursues the cons with complete disregard for the Jailbird staff hostages.
- Vanity License Plate: "AZZ KIKR"
DEA Agent Willie SimmsMolloy's partner who goes undercover so he can glean information from Cindino, but gets caught up in the prison break.
- Hero Antagonist
- Too Dumb to Live: Blows his cover, takes Pinball hostage and tries to single-handedly to take back the plane armed only with a single shot Derringer.
- Villainous Breakdown: He seems at first to be the opposite of Molloy, smooth and calm. That doesn't last long in a crisis.Simms: "I can't control it? I can't control it!?"