Biggest Movie Loser to Ever Get the Girl
AMC Movie List

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 lands one most out of their league?

rank title points votes your vote
1 Andy Stitzer (Steve Carell) in The 40 Year Old Virgin
<p>With social skills as lacking as his sexual experience, Carell does way too well for himself here.</p> 36 84
2 Stu Price (Ed Helms) in The Hangover
<p>The nerdiest guy (Helms) inexplicably gets the hottest girl (Heather Graham) to marry him.</p> 24 78
3 Ben Stone (Seth Rogen) in Knocked Up
<p>Overweight, unemployed and high is apparently enough to make Katherine Heigl swoon.</p> 22 80
4 Daniel Larusso (Ralph Macchio) in The Karate Kid
<p>Among <i>The Karate Kid</i>'s (1984) many plot holes is why Elisabeth Shue would ever go for friendless Daniel-San.</p> 21 67
5 The Geek (Anthony Michael Hall) in Sixteen Candles
<p>Hall's a super-nerd and Molly Ringwald’s a super-babe. Yet he drives off with her in the end.</p> 20 72
6 Jack Dawson (Leonardo DiCaprio) in Titanic
<p>Leo's dirty, skinny, poor and he almost gets Kate Winslet killed. Yet she loves him anyway.</p> 11 85
7 Will Turner (Orlando Bloom) in Pirates of the Caribbean
<p>Keira Knightley leaves her comfortable life for that whiny pansy? Really?</p> 11 79
8 Oz Oseransky (Matthew Perry) in The Whole Nine Yards
<p>Perry's awkward dentist somehow gets a beautiful Mafia babe (Natasha Henstridge).</p> 3 53
9 Rob Gordon ( John Cusack) in High Fidelity
<p>If this movie is to be believed, every pretty and successful lawyer just wants a broke man-child who cheats.</p> 1 57
10 Alvy Singer (Woody Allen) in Annie Hall
<p>Allen plays a nerdy curmudgeon, but he still lands the beautiful Annie (Diane Keaton).</p> -2 64