Round 1: Match 19
Chasing Amy
Arguably the best romantic comedy of all time (this or Say Anything). Proof that not all romantic comedies are brainless sugarjobs for teen girls and house wives to gush over.
VS
Rear Window
Another Jimmy Stewart classic, this one I'd put even above Vertigo. Excellent use of setting, very nice camera work, and Stewart totally carries the movie, while wearing the leg cast, no less.