Across the span of his decades-long career in Hollywood, Rob Reiner directed a host of beloved films—the kind you watch again and again, finding something new in them each time.

As a director, Reiner had immense creative range, from his feature directorial debut mockumentary This is Spinal Tap to the coming-of-age drama Stand By Me to the Oscar-nominated courtroom thriller A Few Good Men to the iconic romantic comedy When Harry Met Sally… and beyond. But what united his work was its deep humanity: a heartfelt humor and tenderness that coursed through each story regardless of genre.

As we mourn the tragic recent deaths of Reiner and Michele Singer Reiner, his wife of 36 years, we look back on some of the many culture-defining films from the Emmy-winning actor and director’s career.

This is Spinal Tap (1984)

Reiner’s feature directorial debut, This is Spinal Tap, is a mockumentary comedy film that follows Spinal Tap, a once-great English heavy metal band, as they embark on a U.S. tour to promote their new album. Known for its spot-on satire of rock documentaries and iconic quotes, Reiner picked up the story again in 2025, with Spinal Tap II: The End Continues. – Anna Grace Lee

Stand By Me (1986)

Based on a Stephen King novella, Stand By Me stars Wil Wheaton, River Phoenix, Corey Feldman, and Jerry O’Connell as four friends who set out to find the body of a boy who was hit by a train. It captures the bittersweet in-between of being a kid, taking place on Labor Day weekend in 1959, as the boys are about to start junior high. As Gordie says, “I never had any friends later on like the ones I had when I was 23. Jesus, does anyone?” – A.G.L.

The Princess Bride (1987)

Full of endlessly quotable lines, The Princess Bride is a fairytale adventure comedy that follows Buttercup, one of the world’s most beautiful women, and her one true love, Wesley, as he must rescue her from a forced marriage to an evil prince. – A.G.L.

When Harry Met Sally (1989)

Written by Nora Ephron, When Harry Met Sally… is one of the best romantic comedies of all time. Harry and Sally are friends who meet on a cross-country drive from college at the University of Chicago to New York City, and later become something much more. Known for its iconic Katz’s Delicatessen scene (in which Reiner’s real-life mother, the actress Estelle Reiner, delivers the much-repeated line, “I’ll have what she’s having”), it’s simply a perfect film. It is also the genesis of another love story: that of Reiner and his wife, Michele. They met on the set of the film, and falling in love with her inspired Reiner to change the ending of the film so that Harry and Sally would end up together. – A.G.L.

Misery (1990)

It’s never easy to adapt a bestselling book into a film that captures what made the original so popular, but Reiner more than completed that assignment with his 1990 adaptation of Stephen King’s 1987 novel Misery. A screenplay by William Goldman and a star-making turn from Kathy Bates as sadistic stalker Annie Wilkes made this psychological horror film iconic, but none of it would have come together into such a chilling portrait of fandom gone wrong without Reiner’s subtle yet increasingly tension-laden direction. – Emma Specter

A Few Good Men (1992)

This legal drama is best known for being one of Aaron Sorkin’s earliest and most popular projects (indeed, the 1992 film was an adaptation of Sorkin’s 1989 play of the same name), but it also launched a partnership between Sorkin and Reiner that continued three years later when Reiner signed on to direct Sorkin’s political rom-com The American President. Upon rewatching A Few Good Men, it’s easy to see why the two men worked so well together; Sorkin’s dialogic pyrotechnics are offset by the genuine curiosity about human behavior and group dynamics that Reiner displayed behind the camera. – E.S.

Flipped (2010)

This late-aughts love story about two neighbors missing—and then finding—their moment for romance was yet another example of Reiner’s facility with the romantic-comedy genre. Although it didn’t receive the kind of universal acclaim that When Harry Met Sally did (to be fair, what film ever could?), Flipped saw a resurgence in popularity in recent years as viewers came to appreciate its naturalistic dialogue and credit it with cult-favorite status. – E.S.