You love to hate them, you hate to love them. There is an irresistible quality to the bad men in film, whose dastardly ways lure you in and keep you rooting for them until the bitter end.

With the remake of 1981’s turbulent Endless Love out this Valentine’s Day, starring Alex Pettyfer as a boy in love with a criminal past, we celebrate some of cinema’s most notorious, sometimes misunderstood scoundrels and their paths to retribution.

John Bender The Breakfast Club

John Bender – The Breakfast Club
Dir. John Hughes, 1985

Spending the majority of John Hughes’ fantastic teen film slumped over a desk and setting things on fire, Judd Nelson’s juvenile Bender is the definition of angst. Criminally minded, troubled and at times malicious, Hughes still urges you not to give up on him, with glimmers of a better person under that grubby coat and a victory that will have you punching the air with him in that famous final shot.

Cry Baby

Cry-Baby – Cry-Baby
Dir. John Waters, 1990

A definitive tale of getting the good girl, Depp is already etching his own iconic status as the greased up Cry-Baby, a juvie graduate with a love of Elvis and misbehaving. Amy Locane’s Allison is the girl to set him straight but not without a social divide, a jealous ex boyfriend and pregnancy scare standing in their way. Waters’ musical is a parody in essence but cements Depp as the irresistible boy from the wrong side of the tracks.

Jim Stark

Jim Stark – Rebel Without a Cause
Dir. Nicholas Ray, 1955

As iconic a wrong’un as you will find, this not only set the bar for misunderstood men everywhere but also became Dean’s most celebrated role. Seventeen and reckless, Stark moves to Los Angeles with his quarrelsome and distant family to find that his troubles have come with him. Falling into rivalry with the local bully and in love with the local sweetheart, his murky past is a reminder that things have to get worse before ultimately get good.

Han Solo

Han Solo – Star Wars: A New Hope, The Empire Strikes Back, Return of the Jedi
Dir. George Lucas, 1977 – 1983

“I know.” The improvised line that Ford shouts back at his princess as he is flung into carbonite is a definitive moment for Solo; arrogant, sincere and assured even in the face of an uncertain fate. It may take a trilogy to map the change in Solo and his allegiance, but the change from a wanted criminal to a rebel hero is an entertaining one.

Patrick Verona

Patrick Verona – 10 Things I Hate About You
Dit. Gil Junger, 1999

Like most of our entries Patrick is an outsider, unkempt and with little concern for those around him. But one musical number later and Heath Ledger has won, not just Kat Stratford’s affections but the unashamed leap from too cool for school to unashamed romantic.

The Driver

The Driver – Drive
Dir. Nicolas Winding Refn, 2011

He can go from a gorgeous kiss with Carey Mulligan to stamping a man’s skull in within mere seconds. This is the epitome of bad to good, moving at the same breakneck speed that The Driver uses for his stunts, and Gosling works his signature muteness to convey a misconceived and unwanting criminal who carries out gruesome deeds for the good of Mulligan’s neighbour and her son.

Chris Chambers

Chris Chambers – Stand By Me
Dir. Rob Reiner, 1986

Of course to anybody watching Stand By Me Chris Chambers is the loyal best friend to Wil Wheaton’s Gordie. To the neighbourhood that Stand By Me is based within however he is the offspring of drunks and criminals, stamping a bad persona onto him which he uses for survival. It’s knowing that Chris’s character is not only good but better in some ways than his friends that make his reputation and fate all the more tragic.

Scott Hastings

Scott Hastings – Strictly Ballroom
Dir. Baz Luhrman, 1992

This spot could easily go to Swayze in Dirty Dancing, but Johnny Castle lacks the self-indulgence of Hastings as he threatens his career and that of his partner in the name his new moves. Mercucio is effortless as the dancer determined to break the rules, and doesn’t stray from his mission even as he falls for his timid new partner. This may be the most sequin clad entry in our list but he’s by no means less determined to win.

Sebastian Valmont

Sebastian Valmont – Cruel Intentions
Dir. Roger Kumble, 1999

Keeping well within the conventions of the teen genre bad boy, this is a manipulative, harsh character with eyes only for his reputation, and in a strange twist his step-sister. Cruel Intentions was one of the more hardcore teen films of the 90s and Ryan Philippe was at the source, smouldering and seducing with abandon. When the error of his ways are realised a cruel twist of fate secures Valmont as an eternal rebel with a destructive legacy.


Alien – Spring Breakers
Dir. Harmony Korine, 2012

Flirting between menace and parody, James Franco is the corn rowed, gold toothed gangster whose bizarre empire is built on years of criminal activity. Seeing potential in four students who dream of a wilder lifestyle, Alien moves from sexual predator to criminal mentor to hopeless romantic in a beautifully entertaining drug fuelled arc, climaxing with a Britney Spears cover.