Playing by Heart (Willard Carroll, 1998)

This is an ensemble romantic film.  It's script has some real corny moments, and a couple of the storylines are underdone.  (Or "underwrought", as one of the characters would say.)  But holy crap, get a load of this cast:

Gillian Anderson:  When this movie came out, she was probably the biggest actress on this list.  I remember an interview she gave on Starz's version of "Inside Hollywood" where Anderson said she was looking for a role that was "as far from X-Files as possible."  Which is extremely ironic, since if you try to imagine Agent Scully in a rom-com - extremely reserved, shy, been "burned" one too many times - then that's pretty much how she appears in this movie.

Angelina Jolie:  Did you know that Jolie was in 15 movies before her breakout role in Girl, Interrupted?!  She was the lead actress in Hackers!  I remember her role in this one pretty well from when I was a kid, including many of her key lines, and I had no idea that she played it until I randomly searched for this movie on Netflix.  And she's excellent - Clare thinks it's her best role ever.  She wears incredibly distracting 90's clothes, but dang if she doesn't sell the part.  Worth watching for her storyline alone.

Jon Stewart!!!:  Liberal millenials, eat your heart out!  Stewart plays the absolute epitome of the rom-com male:  witty and sarcastic, but sweet, and can't take no for an answer.  He's even an architect, if you can believe it.  Even the frosty Anderson can't resist his charms.

Sean Connery:  Okay, this one's actually a little disappointing.  I'm a sucker for late-period Sean Connery with his gravelly voice and excellently manicured white goatee, but at one point he makes a joke about "Intercourse, Pennsylvania" and radio station "WWFU" with his wife played by Gena Rowlands.  (He also makes "little dog panting noises", and that's an image you can't unsee.)

And that's just the tip of the iceberg:  you also get Dennis Quaid (who looks like Clark Kent), Jay Mohr (in an incredibly unfunny role), Ryan Philippe, Madeleine Stowe, and "Goose" himself, Anthony Edwards.  Dang, this movie's a treat.

And even if you're not a 90's actor nerd, it's actually a surprisingly decent movie.