11. Waingro (Heat, 1995)
To borrow a line from Heath Ledger’s incarnation of The Joker, Waingro is an ‘agent of chaos’, but it’s in a manner that is far more vile and depressing than the behaviour of the aforementioned crazy clown. An unrepentant thrill killer and sadist, Waingro needlessly botches a tightly-planned heist when he murders a security guard just for fun, and proceeds to set about causing endless havoc for the main players in revenge for an attempt on his life (because of shit he caused in the first place). To top that off, he is also revealed to be a serial killer of call girls. The film should have won an award for this guy’s Hate Points alone.
12. Dr Christian Szell (Marathon Man, 1976)
What Psycho and Jaws respectively accomplished for showers and the ocean, Marathon Man has gone down in history as doing the same for dentists. A fugitive Nazi war criminal, Szell was notorious for his use of dentistry-inspired torture in concentration camps, and he puts those skills to work upon secretly entering the United States in order to locate his precious cache of stolen diamonds. One of the most terrifying aspects of this eloquent, dead-eyed gent’s behaviour is how utterly methodical he is. I’d hesitate to call him a sadist because he appears to be indifferent to everything except his coveted gems. You’ll never think of the innocent term ‘Is it safe?’ in the same way again.
13. Ben (Man Bites Dog, 1992)
Barking Bonkers Belgian Brutality. That’s an alliterative summary of the exploits of Ben, the disquietingly warped protagonist of this groundbreaking and thoroughly controversial black comedy. A passionate and erudite man, Ben loves poetry, waxes lyrical about the detriment that modern architecture and permissive societal attitudes have had on Belgian culture, and has a penchant for fine cuisine and artisanal booze. He is also a professional thief and serial murderer, and his horrific workdays are being documented by an initially observant film crew who become increasingly more enraptured by his sick life philosophy. Seriously, strap yourself in for this one.
14. J.J. Hunsecker (Sweet Smell Of Success, 1957)
This jealous control freak rules New York City with an iron fist via his nationally syndicated gossip column. With an army of press agents, politicians and even a corrupt cop or two, Hunsecker makes or breaks reputations and careers on a whim, and his tyrannical paternalism towards his younger sister Susan is so extreme that he is prepared to have her boyfriend framed as a dope-smoking Communist (and tarnish the young man’s burgeoning career as a jazz guitarist), purely because he doesn’t like him very much. As vile as he is, watching him intimidate the even sleazier press agent Sid Falco does have a twistedly gratifying effect.
15. Shack (Emperor Of The North, 1973)
This proud, cruel and cunning railroad conductor will see hell freeze over before he ever allows anybody to ride his train for free, especially the many hobos scattered throughout the area. As the head honcho of a freight train operating on an Oregon transport line, Shack has an array of brutal makeshift weaponry that he uses to terrify, beat and murder any unlucky transient that he catches sneaking on board. An irascible bully, he is nevertheless a tough cookie, giving no thought to backing down from a confrontation with Lee Marvin’s legendary tramp A-No.1, the only bum willing to take Shack on.
16. Harold Shand (The Long Good Friday, 1980)
One of the many wonderful treats for the audience when viewing this crime classic is the immediate quandary they are forced into, unsure of whether to root for Harold Shand in his quest to solve the mysteries of the worst day of his personal and professional life, or to hope it takes him to hell in a handcart. A card-carrying Thatcherite, this unremittingly selfish and vicious gangster has nothing but contempt for anybody who isn’t self-made, white, from London or simply ‘traditional’ (except his gay best friend Colin and his American Mafia business partners, they get a pass). The one compliment you can give this horrible bastard is that his shadowy rivals are just a little bit worse.
17. Henry (Henry: Portrait Of A Serial Killer, 1986)
You seldom encounter a more thoroughly horrifying character than Our Hero in this notorious independent shocker. A textbook psychopath, Henry brutally murders scores of people, mostly out of compulsion, but also in rage and even self-defence. Nonchalantly lecturing his best friend Otis about the importance of evading the authorities by constantly changing your Modus Operandi, or recalling how he shot his abusive mother to death, Henry becomes bored and pissed off when dealing with anything except sweet killing. To his credit, he is highly intelligent, and cannot abide child abuse or incest. Which is something, isn’t it?
18. Ray (Nil By Mouth, 1997)
If there were an award for Most Realistically Unpleasant Character, then this rough, foul-mouthed and mean-spirited layabout should win it for all time. Featuring in nearly every scene of Gary Oldman’s cinema verite masterpiece, Ray is an Olympics-level alcoholic, doing odd jobs and black market deals to get by (as he isn’t honest or conscientious enough to work for a living, despite his ability to), launching into horrendous verbal tirades against his wife and extended family when he isn’t beating the shit out of them, and just generally being an intolerant and intolerable arsehole. We are privy to several heartbreakingly human moments with him, but get some help man, Jesus.
19. The Butcher (I Stand Alone, 1998)
You could be forgiven for wanting to give this out-of-work horse mutilator a big hug, were it not for how repellent he is. Orphaned as a nipper, he was subsequently abused by priests, robbed of the opportunity to pursue studies and better himself, abandoned by his wife to raise their child, and then tricked into giving up his business by his overly demanding current squeeze. A hard life indeed, but it doesn’t excuse the borderline sadistic racism, misogyny and homophobia that comes pouring out of the sewer in his face, nor the brutal beating of his pregnant girlfriend or seriously creepy fixation with his vulnerable institutionalised daughter. You’ll need a nice, hot shower after this one.
20. Drexl Spivey (True Romance, 1993)
A whiter-than-cream-cheese weirdo who thinks that he’s black, complete with dreadlocks, stereotypical pimp clothing and use of Ebonics. Why wouldn’t you laugh at him? Well, if you did, you’d receive the mother of all hidings at best, and a shotgun blast to the face at worst. This loose cannon procurer and coke peddler couldn’t be more of a lunatic if he tried, and even with the Mafia backing him up, he holds his own in fearlessness, with a talent for violence and intimidation. He’s most certainly the go-to guy for all of the grisly shit you need doing, but definitely not the one for a parley, especially when he’s trying to be at leisure with a succulent Chinese meal.
Stay tuned for more lists of iconic heroes and douchebags and reviews of classic films and new releases, posted every week.