Originally titled The Adventures of King Bastard and the Romulan Child , the largely unlikeable cast is saved by Hugh Grant playing a self-described "emotionally stunted asshole." It's an amazing performance, second only to the time he put Colin Firth through a plate-glass window in Bridget Jones's Diary.
Verdict: Trust us, this one's all about how awesome Grant really is, but the scene where Marcus shuffles through school singing "Shake Ya Ass" by Mystikal might just be the funniest thing in the entire movie.
Cracked Fact: As recently as 2003, filmmakers still thought it was a good idea to end on a freeze-frame of a laughing child, despite mountains of evidence to the contrary.
Back before he traded teenage girls for Jake Gyllenhall and a scenic mountaintop view, Heath Ledger caught a break from the late '90s push to make Shakespeare hip for the kids. And since Shakespeare never wrote a story about an ugly girl suddenly becoming beautiful when she takes off her glasses, this one's already one step ahead of every other teen romance.
Verdict: Considering that it's Taming of the Shrew without the puns and set in a high school, it actually works out a lot better than you'd think-although to be fair, Julia Stiles' "I need agua!" would stand as the worse use of Spanish on film until Mind of Mencia 's debut six years later.
Cracked Fact: Even if you're single, you may want to keep in mind that there's a scene in this one where an 18-year-old Stiles performs a drunken table dance at a high school beer bash. Just puttin' that out there.
The DVD's box art is almost exactly the same as 2003's How To Lose A Guy In 10 Days, but this one manages to avoid being anywhere near as derivative as, well, anything Richard Gere's done since Pretty Woman. Instead, it offers up sharp writing, slapstick comedy and the occasional animal attack-and while those aren't the standard ingredients for romance, they should be.
Verdict: The main plot might be faintly ridiculous, but a cameo appearance by Patton Oswalt and a laugh-out-loud hilarious scene where Zooey Deschanel tries to buy a shotgun from The Daily Show's Rob Corddry push it to must-see status.Cracked Fact: Except for that one time that he fought dragons, Matthew McConaughey's essentially been playing Wooderson from Dazed and Confused for thirteen years.
ALSO UNDERRATED: Love Actually, Bridget Jones's Diary