Rob Reiner’s Most Iconic Movies: From When Harry Met Sally to The Princess Bride

Few filmmakers in Hollywood history have built a career as versatile, emotionally resonant, and enduring as Rob Reiner. Seamlessly moving between romantic comedy, courtroom drama, psychological thriller, and coming-of-age storytelling, Reiner has crafted some of the most beloved films of the past four decades—movies that continue to shape popular culture long after their release.

When Harry Met Sally (1989): Redefining Romantic Comedy

Reiner’s most culturally influential film, When Harry Met Sally, didn’t just entertain audiences—it redefined the modern romantic comedy. Inspired in part by Reiner’s own experiences navigating single life for nearly a decade, the film explored whether men and women could truly remain “just friends.”

Originally, the script did not even end with Harry and Sally together. That changed after Reiner met his future wife, Michelle, during production—an off-screen love story that reshaped the film’s iconic ending.

The movie also delivered one of cinema’s most famous scenes: Meg Ryan’s unforgettable diner performance, capped by the legendary line, “I’ll have what she’s having,” spoken by Reiner’s real-life mother, Estelle Reiner. Billy Crystal later called it the funniest line of his career.

The Princess Bride (1987): A Timeless Fantasy Classic

If When Harry Met Sally captured adult love, The Princess Bride captured childhood wonder. A perfect blend of fantasy, romance, comedy, and adventure, the film has become a multi-generational classic, endlessly quoted and adored.

Reiner’s father, legendary comedian Carl Reiner, once named The Princess Bride as his favorite film directed by his son—a meaningful endorsement from one Hollywood icon to another.

Stand by Me (1986): A Story of Friendship and Growing Up

With Stand by Me, Reiner delivered one of the most honest and emotionally powerful coming-of-age films ever made. Based on a Stephen King novella, the movie explored friendship, loss, and mortality through the eyes of four boys on a life-changing journey.

Decades later, the film remains a touchstone for audiences reflecting on youth, memory, and the moments that quietly shape who we become.

Misery (1990): Psychological Terror at Its Finest

Reiner proved his range again with Misery, a chilling psychological thriller that earned Kathy Bates an Academy Award for her terrifying performance. The film showed Reiner’s ability to create sustained tension without spectacle—relying instead on character, dialogue, and atmosphere.

A Few Good Men (1992): Courtroom Drama at Its Peak

One of Reiner’s most critically acclaimed films, A Few Good Men delivered unforgettable performances and one of cinema’s most quoted lines: “You can’t handle the truth.” The film earned Reiner an Oscar nomination as a producer and remains a benchmark for courtroom dramas.

The Bucket List (2007): Facing Mortality with Heart

Later in his career, Reiner directed The Bucket List, starring Jack Nicholson and Morgan Freeman as terminally ill patients who escape their hospital ward to fulfill lifelong dreams. The film reflected Reiner’s growing contemplation of mortality and the importance of saying what needs to be said to those we love.

Beyond the Director’s Chair

While best known as a director, Reiner has also enjoyed a successful acting career—from his breakout role as “Meathead” on All in the Family to memorable appearances in The Wolf of Wall Street, where he played Leonardo DiCaprio’s concerned father.

A Lasting Legacy

Rob Reiner’s greatest achievement may be his emotional range: films that make audiences laugh, cry, reflect, and feel understood. Whether through romance, fantasy, drama, or humor, his work continues to remind viewers of the power of honest storytelling—and why some movies never fade, no matter how much time passes.