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
Once the success of When Harry Met Sally made her a multi-kajillionaire, Nora Ephron turned over actual writing duties to the ScripTron 9000 robot, which produced this charming formula: Cute quirky girl meets cute quirky guy and, despite various factors keeping them apart, they fall in love, ditch their respective mates and end up together in just under two hours. SEE ALSO: Every single romantic comedy made in the 1990s.
Verdict: It may be responsible for dozens of knock-offs-including one where Meg Ryan's romanced by a time-traveling Hugh Jackman and another that's built around the somewhat creepy notion of sex by email leading to a fulfilling relationship-but it does have its brief moments where you won't want to punch the cute out of someone.
Cracked Fact: For Tom Hanks, this flick was just a stepping-stone on his way to becoming one of Hollywood's biggest, most bankable stars. Meg Ryan? She's pretty much still doing this.
One of the vilest monstrosities ever committed to film. The "romance" aspect centers around our jealous, stalker-esque protagonist (Julia Roberts) and her attempts to utterly ruin the lives of people who have achieved happiness while she remains alone and, with good reason, unloved. As for the alleged comedy, it falls somewhere between Corky Romano and Schindler's List.
Verdict: Romances centered around a thoroughly reprehensible protagonist that still manage to be fun and entertaining are incredibly difficult to pull off, as evidenced by the fact that this attempt failed miserably.
Cracked Fact: Oddly enough, Julia Roberts was a lot more likeable when she having sex for money in Pretty Woman.
Who would've thought that a crime-themed romantic comedy from the stars of Reindeer Games and Anaconda would turn out so unbelievably horrible? You know, aside from the movie-going public.
Verdict : If you're TV surfing at two in the morning and catch the scene where Jennifer Lopez threatens to rip someone's eye out while a heavily-accented Ben Affleck snaps a guy's laptop in half while shouting "www-dot-suck-my-dick-dot-com!", it briefly and unintentionally becomes the most hilarious movie ever made. Any longer than that and you'll reflexively claw your own eyes out.
Cracked Fact: Many box-office flops like Ishtar and Waterworld aren't as bad as their reputations would lead you to believe. Seriously, though: Gigli fucking blows.
ALSO TOTAL CRAP: I Love Trouble, Runaway Bride
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