Skip to main content

50 Worst Movie Ex-Boyfriends

Harry Lime (The Third Man)

The Ex-Boyfriend: Boyfriend of actress Anna, racketeer Harry Lime (Orson Welles) dies in a traffic accident...

His Post-Break-up Behaviour : Well, supposedly death parts them. That is until Harry returns, lurking outside Anna's apartment just as the full exposure of his crimes of selling watered-down penicillin are being revealed.

Waldo (The Little Rascals)

The Ex-Boyfriend: Putting the boy into ex-boyfriend is Waldo, the wealthy and obnoxious suitor of Darla. Waldo frequently plays dirty in attempt to keep rival Alfalfa out the game, this includes talent show sabotage.

His Post-Break-up Behaviour: Darla soon tires of Waldo's attitude and dirty tricks and tells him so during the annual go-cart race. He reacts by abandoning her on the side of the road and driving off.

Dexter (One Day)

The Ex-Boyfriend: Privileged and good-looking Dexter (Jim Sturgess) briefly hooks up with geeky Emma (Anne Hathaway) on the eve of their university graduation.

His Post-Break-up Behaviour: Their graduation fling marks the beginning of a long will they/won't they friendship between the pair. Dexter gets it together in the end, but only after he becomes an arrogant drunk, demeans Emma's profession and is an all-round, general arse. In all honesty, Emma could do better.

Rob Gordon (High Fidelity)

The Ex-Boyfriend: Record store owner and music geek Gordon (John Cusack) is particularly bad at understanding women.

His Post-Break-up Behaviour: Rob is dumped by Laura because of his lack of commitment. Instead of getting his act together, he spends his time mooching around creating lists and re-exploring what went wrong with his past relationships.

Hardy Jenns (Some Kind Of Wonderful)

The Ex-Boyfriend: Hardy Jenns looks like a sleazy member of Duran Duran and frequently cheats on the hottest girl in school Amanda Jones (Lea Thompson).

His Post-Break-up Behaviour: At the end of her tether, Amanda dumps Hardy and accidentally stumbles into the arms of awkward loser Keith (Eric Stoltz). Hardy reacts by attempting inflict a mass party beating upon Amanda's new man and forcing her to beg him to take her back.

Sack Lodge (Wedding Crashers)

The Ex-Boyfriend: Aggressive and controlling Sack Lodge is only dating Claire because of her father's political power. He cheats on her and announces the couple's engagement before even asking for her hand.

His Post-Break-up Behaviour: Sack is left standing at the altar when Claire realises how bad he is. Sack handles this by aggressively demanding the wedding the should continue and attacking Claire's alternative suitor John.

Eirik (In Bruges)

The Ex-Boyfriend: Eirik is the very angry ex-boyfriend of Chloe (Clemence Poesy) who doesn't take kindly to her being romanced by rookie hitman Ray (Colin Farrell).

His Post-Break-up Behaviour: Unlucky Eirik is ditched by Chloe and also gets shot in the eye when he attempts to take out Ray. Ouch.

Curtis Taylor Jr (Dreamgirls)

The Ex-Boyfriend: Jamie Foxx is Curtis Taylor Jr, a smooth and suave Cadillac dealer-turned-record executive who takes on the Dreamettes and propels them to stardom while leading on front-woman Effie (Jennifer Hudson).

His Post-Break-up Behaviour: Not only does Curtis send Effie packing romance-wise, but he writes her out the group replacing her with his secretary. He then marries her slimmer more marketable band-mate Deena (Beyonce Knowles).

Alex Linden (Bad Timing)

The Ex-Boyfriend: Alex Linden is an psychiatrist who becomes involved with the young, free spirited and married Milena.

His Post-Break-up Behaviour: Alex becomes fed up of not being the only man in Milena's life. She turns down his marriage proposal, tiring of him stalking her and trying to control her. She later calls him during a suicide attempt. He arrives and disturbingly takes advantage of her semi-conscious state...

Martin (Sleeping With The Enemy)

The Ex-Boyfriend: Martin is wealthy investment councillor who breaks out the jealousy, possessiveness and physical abuse as soon as he has a wedding ring on Laura's (Julia Roberts) finger.

His Post-Break-up Behaviour: Naturally Laura attempts to escape Martin and she does this in a hilariously elaborate series of events. However, Martin is not a man who gives up easily. He hunts her down and tries to kill her.