Samuel Walters wrote:
If you're going to watch When Harry Met Sally, you should see its 90s counterpart Sleepless In Seattle. Toss in You've Got Mail and you've got a nice Billy Crystal - Meg Ryan movie marathon night.
Except that the last two were Tom Hanks/Meg Ryan movies
But Harry & Sally is the quintessential relationship comedy that everyone should have seen because it really hits the truth at times.
So far most movies mentioned here would have been on my list too, small addition though:
The Siege (a bit relevant movie for the post 9/11 era)
Mr. Holland's Opus (awesome movie about an at first unwilling music teacher and how he influenced his students and in return was influenced by them)
Stakeout (awesome cop/comedy/romantic movie)