Let's talk about this movie right quick. Just the ticket when you need to take a hot steaming cry-dump.
Old buddies. All those TV sitcom royalty cameos: Lisa "I'm a motherfucking Cosby" Bonet and Melissa "I grew up on a rad plaid couch" Gilbert?! So comforting to see them grownupish. Also, Alex Desert of Hepcat & Boy Meets World fame, in his forgettable role as Louis the customer.
Chicago. Chicago is such a perfect romantic backdrop. All that rain, that lushness. Parks to fight and fuck in. All those bars for drowning sorrows and trains for lamenting. Perfect.
Rings. The horrible new fling Ian (with an 'I'--by the way), deftly played by Tim Robbins, has a ponytail and wears rings on his fingers. Totally hateable. I never could get on board with John Corbett in Sex & the City, because his Aiden character was too gooey in the same vein.
"That guy*." R worked at a record store for near a decade. After the movie came out, people would come in and tell his coworker, "HEY! You look exactly like that guy from High Fidelity!" It really got under his skin. He did, but Jack Black was skinnier and more charming.
Casting. In addition to TV princesses, casting IRL ex, Lili Taylor and IRL sister, Joan Cusack. I like Joan's face. It's looks like one of those creepy smiling mannequins mated with a blow up doll.
Sigh. It never fails to make me bawl and want to wear choker necklaces.
*Please don't be that guy and say, "the book was better**."
**Even if it was, ok?