The Truman Show (1998) Jim Carrey, Laura Linney, Ed Harris. This is so a guilty pleasure of mine. Seriously, who doesn't stop and wonder if maybe they're constantly being watched? Please don't tell me it's only me. Oh. Hmm. Awkward.
Pretty in Pink (1986) Molly Ringwald, Jon Cryer, James Spader. This movie came out the year I was born and the outfits are hilariously ridiculous and I'm totally willing to admit I have a huge crush on Duckie. The fact that Jon Cryer is now middle aged and on Two and a Half Men, this does not keep me from harboring a huge crush on him circa 1986. Stop looking at me like that.
The Virgin Suicides (1999) Kirsten Dunst, Josh Hartnett, James Woods. This is the only movie I have ever seen that I have also read the book and loved both, despite their totally different endings. I have already forced most of my friends to watch this so somehow I don't see many people asking to borrow this.
As Good as it Gets (1997) Jack Nicholson, Helen Hunt, Greg Kinnear. Another movie I have come to love thanks to my dad. To this day he still quotes Jack Nicholson and yearns for a little rat-dog he can call Verdell.
Where the Heart is (2000) Natalie Portman, Ashley Judd. This was the first movie I had ever seen with Natalie Portman (save for Star Wars, natch) and the fact that parts were moving enough to make my big manly dad cry in the movie theatre totally made the 15 bucks for the DVD worth it. Seriously, he wouldn't let us leave the theatre until he pulled himself together. Sucker.
