Biggest Movie Loser to Ever Get the Girl

Guys like Woody Allen and The Karate Kid are always landing women who are out of their league. Who's most out of their depth?

rank title points votes your vote

1 Anthony Michael Hall
In Sixteen Candles (1984) he's a super-nerd and she's a super-babe. Yet he drives off with her in the end. 33 83

2 Steve Carell
With social skills as lacking as his sexual experience The 40 Year Old Virgin does way too well for himself. 27 83

3 Seth Rogen
Overweight, unemplyed and high is apparently enough to make Katherine Heigl swoon in Knocked Up (2007). 23 85

4 John Cusack
If High Fidelity (2000) is to be believed, every pretty and sucessful lawyer just wants a broke man-child who cheats. 10 68

5 Ed Helms
In The Hangover (2009) the nerdiest guy (Helms) gets the hottest girl (Heather Graham). 6 64

6 Ralph Macchio
Among The Karate Kid's (1984) many plot holes are why Elisabeth Shue would ever go for friendless Daniel-San. -1 67

7 Matthew Perry
Perry's nerdy dentist in The Whole Nine Yards (2000) somehow gets a beautiful Mafia babe (Natasha Henstridge). -2 70

8 Leonardo DiCaprio
In Titanic (1997) he's dirty, he's poor and he almost gets Kate Winslet killed. Yet she loves him anyway. -6 76

9 Woody Allen
In Annie Hall, he's a nerdy curmudgeon, but he still lands the beautiful Annie (Diane Keaton). -7 75

10 Orlando Bloom
Keira Knightley leaves her comfortable life in Pirates of the Caribbean for that whiny pansy? Really? -8 80