Playing by Heart is a 1998 romantic drama film directed by Willard Carroll. It follows the lives of eleven Los Angeles residents as they navigate through relationships and affairs of the heart.
Among the characters are Hannah (played by Gillian Anderson), a successful TV chef whose on-screen persona hides her personal insecurities; Paul (Sean Connery), Hannah's producer and father figure, who harbors a secret love for her; and Mark (Ryan Phillippe), a young man dying of AIDS who forms a close bond with his mother (Angelina Jolie) as he faces his mortality.
Meanwhile, Meredith (played by Madeleine Stowe) is a jaded career woman who has been burned by love and avoids commitment, until she meets Trent (Anthony Edwards), a persistent and charming architect who slowly wins her over. Keenan (Dennis Quaid) is a lonely theater director who is drawn out of his shell by the lively and verbose Joan (Angelina Jolie), who is herself struggling with her own issues of self-worth and identity.
In addition to these main storylines, the film also includes secondary characters, such as the married couple Roger (Sean Connery) and Mildred (Gena Rowlands), who carry on a heated affair at various hotels around town; and Hugh (Dennis Hopper), a compulsive liar who tells tragic stories to women he meets in bars.
The film weaves these various stories together with humor, pathos, and a touch of whimsy, culminating in a poignant and emotionally satisfying finale. With its star-studded cast and well-crafted ensemble narrative, Playing by Heart is a thoughtful and touching examination of love, loss, and human connection.