From Zabka to Zane: The 'Best' Bastard Boyfriends in Movies

Why are girls always attracted to jerks? It’s become a standard trope in the movies, but it’s one that any “nice guy” will agree rings true. Boyfriends (or jealous ex-boyfriends) of the film’s love interest are sure to be some combination of three characteristics: wealthy, snobby, unfaithful. While he may not be quite as bad as most, there’s another of the model coming off the assembly line in the new Daniel Radcliffe-Zoe Kazan romantic comedy, What If, this time played by Rafe Spall.

In real life, we hate them. In the movies, we also hate them, but applaud their fearless performances. Here are the 10 best actors who have been their best while being the worst boyfriends.


10. Craig Kilborn, Old School (2003)
Jerk of All Trades: Mark, the very tall and very smarmy boyfriend of Mitch’s (Luke Wilson) object of affection, Nicole (Ellen Pompeo).
Typical Boorish-Boyfriend Behavior: Cheats on Nicole with a caterer in a bathroom at a kid’s birthday party.
Prime Put-Down: “What are you gonna do? Tell on me? You know you can’t, buddy. It’s guy code. Guys don’t tell on other guys. That’s something chicks do. You’re not a chick, are you?”
Comeuppance: Dumped (offscreen).

9. Anthony Michael Hall, Edward Scissorhands (1990)
Jerk of All Trades: The beer-muscled Jim, boyfriend to Kim (Winona Ryder).
Typical Boorish-Boyfriend Behavior: Frames Eddie Scissorhands (Johnny Depp) for burglary, repeatedly tries to attack him.
Prime Put-Down: “Go you freak!”
Comeuppance: Dumped, and then pushed out a window, where he falls to his death.

8. Ben Affleck, Mallrats (1995)
Jerk of All Trades: Dim-witted ‘Fashionable Male’ mall-store manager Shannon Hamilton, boyfriend of (Shannen Doherty) and nemesis to Brodie (Jason Lee).
Typical Boorish-Boyfriend Behavior: Has sex with an underage girl
Prime Put-Down: “I have no respect for people with no shopping agenda.”
Comeuppance: Gets cheated on, dumped and arrested for statutory rape.

 7. Craig Sheffer, Some Kind of Wonderful (1987)
Jerk of All Trades: Hardy Jenns, the rich, Corvette-driving ex-boyfriend of Amanda (Leah Thompson).
Typical Boorish-Boyfriend Behavior: Refers to his girlfriend as “his property,” cheats on her, and then arranges a whole house party just so he can beat up Keith (Eric Stoltz).
Prime Put-Down: “I want you to beg.”
Comeuppance: Dumped, and humiliated at his own house party when school tough guy Duncan (Elias Koteas) and gang show up to “wipe the floor with his ass.”


6. Jason Schwartzman, Scott Pilgrim Vs. the World (2010)
Jerk of All Trades: Pretentious club owner/music exec Gideon Graves, the most evil of Ramona’s (Mary Elizabeth Winstead) seven evil exes whom Scott Pilgrim (Michael Cera) must defeat.
Typical Boorish-Boyfriend Behavior: Plants mind control devices in his girlfriend’s head.
Prime Put-Down: “Well, if my cathedral of cutting-edge taste holds no interest for your tragically Canadian sensibilities, then I shall be forced to grant you a swift exit from the premises… and a fast entrance into hell!”
Comeuppance: Defeated.

5. Jim Youngs, Footloose (1984)
Jerk of All Trades: Good ol’ boy Chuck Cranston, who makes Ren’s (Kevin Bacon) new life in the country even tougher.
Typical Boorish-Boyfriend Behavior: Beats up girlfriend Ariel (Lori Singer), insists on settling disputes with tractor chicken.
Prime Put-Down: “I thought only pansies wore neckties.”
Comeuppance: Dumped. Also misses out on a great dance party.

4. Matthew Glave, The Wedding Singer (1998)
Jerk of All Trades: Snotty rich businessman Glenn Gulia, about to marry Julia (Drew Barrymore), therefore resulting in the awful name Julia Gulia.
Typical Boorish-Boyfriend Behavior: Regularly cheats on Julia, and makes it clear to Robbie (Adam Sandler) he has no intention to stop.
Prime Put-Down: “Hey, asswipe, don’t go snitching to Julia about this. I know you got a little crush on her, but you gotta face the facts: she’d rather go to bed with a REAL man. Not some poor singing orphan.”
Comeuppance: Dumped, and also humiliated by Billy Idol on an airplane.

3. Bradley Cooper, Wedding Crashers (2005)
Jerk of All Trades: Ivy League snob Zack Lodge, who only dates Claire (Rachel McAdams) because of her dad’s political power.
Typical Boorish-Boyfriend Behavior: Regularly cheats on and mocks Claire, takes a friendly game of football way too seriously, and is just overall insufferable.
Prime Put-Down: “Big tree fall hard, right?”
Comeuppance: Gets wine spiked with eye drops, which have a laxative effect, and of course, dumped.

2. William Zabka, Karate Kid (1984)
Jerk of All Trades: Johnny Lawrence, the Cobra Kai captain and jealous ex of Ali (Elizabeth Shue), who fights Daniel-San (Ralph Macchio) all kinds of dirty. (See also any other Zabka movie from the ’80s.)
Typical Boorish-Boyfriend Behavior: Jump Daniel on Halloween.
Prime Put-Down: Here’s your first lesson. How to take a fall!
Comeuppance: Defeated with that one sweet kick.

1.   Billy Zane, Titanic (1997)
Jerk of All Trades: Caledon ‘Cal’ Hockley, the rich and snobby (stop us if you’ve heard this before) older boyfriend to Kate Winslet’s Rose.
Typical Boorish-Boyfriend Behavior: Frames Jack (Leonardo DiCaprio) for theft; Tricks Rose into boarding the lifeboat.
Prime Put-Down: “ Where are you going? To him? To be a whore to a gutter rat?”
Comeuppance: Dumped. And while he gets off the boat safely, but it’s later revealed he committed suicide when he lost his fortune in the stock market crash.

Honorable Mentions:

Aaron Dozier, Better Off Dead (1985)
Steve Antin, The Goonies (1985)
George Gray, Can’t Buy Me Love (1987)
Peter Facinelli, Can’t Hardly Wait (1998)
Daniel Cosgrove, Van Wilder (2002)

Photos: CBS, DreamWorks, Miramax, Paramount, Everett (6)