50 Worst Movie Ex-Boyfriends

Joseph (Amelie)

The Ex-Boyfriend: Joseph is one of the many eccentric regulars at the Cafe des demux Moulins, who harbours very strong stalkerish tendencies.

His Post-Break-up Behaviour: Joseph is ditched by two different waitresses at the Cafe yet he continues to eat there, menacingly narrating the girls' every move to his dictaphone.

Dom 'Woogie' Woganowski (There's Something About Mary)

The Ex-Boyfriend: Dom 'Woogie' Woganowski was the high-school boyfriend of Mary who got 'weird' on her back in the day and tends to develop nervous hives just thinking about her.

His Post-Break-up Behaviour: Mary dumps Woogie in High School so thirteen years later he becomes the best friend of Mary's one-time prom date Ted and encourages Ted to hire a private investigator to track Mary down so he can break his restraining order and steal her shoes.

David (Endless Love)

The Ex-Boyfriend: Teenagers David and Jade fall madly in love and form an intense, all-consuming relationship which has a detrimental effect on Jade's school work.

His Post-Break-up Behaviour: After Jade's dad tries to keep the pair apart, David burns down her family's house. This sends him to a mental hospital for two years. On release, he attempts to pursue Jade once again, causing the death of her father in the process.

Jimmy Angelov (Practical Magic)

The Ex-Boyfriend: Handsome Bulgarian Jimmy is a tad too obsessive and possessive over his girlfriend Gillian (Nicole Kidman). His habits include wanting the pair to go to the bathroom at the same time and branding her with his skull ring.

His Post-Break-up Behaviour: Gillian leaves Jimmy so he responds by kidnapping her and her sister and trying to strangle her to death. Unfortunately for Jimmy, Gillian and her sister are witches and accidently posion him. However, after the witches kindly bring him back to life he attempts to kill them again. Well, that's just rude.

Jackie Boy (Sin City)

The Ex-Boyfriend: Jackie Boy (Benicio del Toro) is violent drunk who skips out on his wife to pursue waitress Shellie (Brittany Murphy).

His Post-Break-up Behaviour: Shellie ends things with Jackie Boy after he roughs her up, but that doesn't stop him hammering at her door with a group of henchmen and accusing her of 'playing hard to get'.

Anakin Skywalker (Star Wars)

The Ex-Boyfriend: Jedi Knight Anakin is the "Chosen One", a hero of the Clone Wars with a beautiful pregnant wife (Natalie Portman).

His Post-Break-up Behaviour: Anakin's other half, Padme, decides she wants out when she realises he is actually slaying children and quickly drifting to the dark side. Anakin deals with this by using the force to strangle her and eventually becoming Darth Vader, one of the most evil men in the whole galaxy.

Gideon Graves (Scott Pilgrim vs. the World)

The Ex-Boyfriend: Gideon Graves is the sponsor of Scott Pilgrim's band and also the leader of the league of the evil ex-boyfriends of Scott's girlfriend Ramona Flowers.

His Post-Break-up Behaviour: Gideon does not like being out of Ramona's life. Not only does he effectively force her new man to leave his band The Sex Bo-Bombs, but Gideon is also influencing his ex-girlfriend's behaviour with a mind control device in the back of her head. Evil!

Jason Dean (Heathers)

The Ex-Boyfriend: High school student Veronica develops the hots for rebellious loner J.D. when he pulls a gun on a group of school bullies and kills her bitchy, popular best friend Heather.

His Post-Break-up Behaviour: Veronica calls it quits with J.D. when his pure evil becomes a little too much for her to handle. He reacts by attempting to kill her and blow up the school.

Charlie Venner (Straw Dogs)

The Ex-Boyfriend: Charlie is a Wakey local who harbours an obvious resentment towards his ex-lover's new husband.

His Post-Break-up Behaviour: Not impressed he has been replaced with intellectual mathematician David, Charlie doesn't make things easy for the couple. His ex-boyfriend crimes are endless and extreme: he intimidates and taunts them both, kills their cat, and eventually rapes Amy.

David (Fear)

The Ex-Boyfriend: Charming and sweet David sweeps native teen Nicole off her feet when the two meet at a rave.

His Post-Break-up Behaviour: After he gives her a black eye and forces himself on her friend, Nicole decides to call it a day with David. David reacts by smashing up her dad's car, carving her name into his chest, beheading her dog and trying to kill her family. Smooth.