The 30 best romantic comedy movies, ranked 26. Playing by Heart (1998)

Not strictly a romantic comedy, buoyed as it is by serious drama involving everything from infidelity to AIDS, Playing by Heart is one of those talky, interconnected, Robert Altman-esque indies that dominated so much of American cinema in the Nineties. But the reason it’s here is because two of its many storylines feature lighter pairings that appear unlikely on paper but somehow become incredibly compelling and tender in execution. In one, Angelina Jolie and Ryan Phillippe meet at an LA bar and begin a romance; in another, Gillian Anderson and Jon Stewart meet in a bookstore and begin dating. Both stories develop from there, with Sean Connery, Gena Rowlands, Ellen Burstyn and Madeleine Stowe among the recognisable faces orbiting them. But whatever the tone of each seemingly unrelated story, Playing by Heart is driven by a lovely, nostalgic sense of Los Angeles ennui at the end of the 20th century. No one has heard of this movie, and that’s a shame.

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