Playing by Heart is a 1998 romantic dramedy featuring an All-Star Cast. The film follows a number of characters living in Los Angeles and their relationships.

• All-Star Cast: Angelina Jolie, Ryan Philippe, Jon Stewart, Gillian Anderson, Sean Connery, Gena Rowlands, Dennis Quaid, Madeline Stowe, Anthony Edwards, Jay Mohr and Ellen Burstyn.
• Anguished Declaration of Love: Joan makes one for Keenan after he reveals .
• Dark Secret: Keenan avoids getting too close to Joan, until he reveals .
• Drink Order:

• Faux Yay: Hugh attempts this at a gay bar, but the Drag Queen he's chatting to sees through the ruse.

• Fiery Redhead: Joan. Meredith has the red hair, but not the personality.
• The First Cut Is the Deepest: For Keenan, with devestating consequences.
• Happily Married: Paul and Hannah. Averted with .
• Hyperlink Story: The final scenes of the film reveal how the characters are linked-
• Silly Rabbit, Romance Is for Kids: Meredith's view of relationships- after getting hurt one too many times she's reluctant to get involved with Trent.
• Single Woman Seeks Good Man: Joan
• You Gotta Have Blue Hair: Keenan
• Your Cheating Heart: Played straight with who is cheating on with who is also cheating on his spouse.
  • Keenan's first girlfriend cheated on him, .
  • Averted with Paul, who admits to Hannah that he toyed with having an affair with a former co-star in the past, but resisted temptation.