49. You've Got Mail (1998)

Director: Nora Ephron
Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey, Steve Zahn, Dave Chappelle, Jean Stapleton
Lame Love Song: "Anyone at All," Carole King
Love Conquers: E-mail

You've Got Mail's status as the longest infomercial ever is enough to earn the film a spot on the list, as the title itself is an AOL trademark. Shameless shilling aside, this film does not hold up well. The Internet has come a long since the dawn of instant messaging; advances in social media make Internet anonymity much more difficult.

In recent years, the film has become further antiquated, as Tom Hanks's character works for a bookstore mega-chain trying to run poor Meg Ryan out of business. The only reason to go in a bookstore these days is because your e-reader isn't working (or because you love the smell of dead trees). As technology marches forward, this film becomes more and more stale—sort of the opposite of a fine wine.