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The Best Rob Reiner Movies – 10 Movies That Prove He Was A Legend

The best Rob Reiner movies range from timeless crowd-pleasers to Oscar-level drama. Here are the top 10.

Caryn GanessbyCaryn Ganess
December 15, 2025
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Best Rob Reiner Movies

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It’s hard to believe that Rob Reiner’s impressive directing credits won’t have any more masterpieces added to them in the future. The 78-year-old filmmaker and his wife were found dead in their Los Angeles home on Sunday night. With all the tributes pouring in to honour what can only be described as a legendary and wildly versatile career, let’s take a trip down memory lane and revisit some of Rob Reiner’s best movies.

Flipped

Flipped movie 2010
Image Credit: Warner Bros.

Flipped is one of the sweetest—maybe a little cringeworthy—tween-focused romcoms of the noughties.

It tells the story of two young neighbours who have very different perspectives on the events that unfold between them and follows how their feelings towards each other evolve/change with time.

Reiner captures the innocence and awkwardness of young love with incredible charm, no matter how cheesy it can get at times.

The Bucket List

The Bucket List movie
Image Credit: Warner Bros. Pictures

As much as critics tore The Bucket List apart, most regular folk will agree that it’s at least a heartwarming exploration of life, death, and the importance of milking every last moment you’re given for all it’s worth.

Rob Reiner did a great job of bringing his background in comedy to some heavy subject matter.

Was it perfect? Probably not. But it does leave you wanting to make the most of the time you’re given, and I think that was always the goal.

The American President

The American President movie
Image Credit: Columbia Pictures

Michael Douglas plays a widower U.S. President (with a 63% approval rating, imagine that) who falls in love with a fiery environmental lobbyist (Annette Bening) in this Rob Reiner-directed film.

If you’re a fan of Aaron Sorkin’s writing, you’ll probably enjoy this film. Mostly because it has all the typical Sorkin elements. Expect long liberal speeches, some pretty witty dialogue, and a healthy dollop of nostalgic pop culture references. 

But it also has all the makings of a Rob Reiner hit: comedy, romance, and politics, so there’s that.

The Sure Thing

The Sure Thing movie
Image Credit: Embassy Films Associates

Although The Sure Thing wasn’t Reiner’s best romantic comedy, it was still a solid first start.

This love story follows two freshman college students, Alison (Daphne Zuniga) and Gib (John Cusack), on their way to California for winter break. The two catch the same ride-share to The Golden State but end up having to hitchhike together after their lift kicks them out because they just won’t stop arguing.

It’s the typical romcom formula: two teenagers who can’t stand each other at first but are actually perfect for each other in the end. But Reiner and his crew can be applauded for the very honest way they deal with topics like sex in this teen movie.

Misery

The 5 Best (And 5 Worst) Stephen King Movies Misery (1990)
Image Credit: Columbia Pictures

Reiner’s Castle Rock Entertainment secured the rights to Stephen King’s Misery for just one dollar because of how much King loved the filmmaker’s adaptation of his novel The Body. Reiner definitely did King proud once again.

The director took a story not about monsters or ghosts but about a deranged fan and turned it into one of the most chilling horror films of the 90s, and a story that could be even more applicable today than it was back then.

Kathy Bates also did an exceptional job of bringing the character of Annie Wilkes to life and, in turn, landed an Academy Award for Best Actress for her efforts.

When Harry Met Sally…

When Harry Met Sally
Image Credit: Columbia Pictures

There’s a reason why When Harry Met Sally… clocks the top of most romantic comedy lists. Rob Reiner and Nora Ephron did a great job of putting together the details of this slow-burn, friends-to-lovers story.

It all starts when Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a car ride from Chicago to New York City after their college graduation. They meet a few more times along the way before finally reconnecting and becoming actual friends years later.

Of course, things get a bit complicated, but (spoiler alert) we still get the big sappy ending we all want from our romantic comedies.

Stand by Me

Stand By Me (1986)
Image Credit: Columbia Pictures

Stand by Me was as meaningful for Rob Reiner as it was for the millions of viewers who watched it in the 80s.

The coming-of-age story is about four friends, Gordie (Wil Wheaton), Chris (River Phoenix), Vern (Jerry O’Connell), and Teddy (Corey Feldman), who discover where the body of a boy who went missing from a nearby town is and then get the idea to hike out and find it first.

The movie was based on Stephen King’s novella The Body and is still considered one of the best adaptations of King’s work (even by the writer himself).

A Few Good Men

A Few Good Men Jack Nicholson Tom Cruise
Image Credit: Columbia Pictures

Rob Reiner and Aaron Sorkin made one of the most quoted courtroom dramas of all time with A Few Good Men. We’re sure you’ve heard or uttered the line, “You can’t handle the truth!” at least once in your life.

A big part of the movie becoming so memorable is the intense performance by Jack Nicholson and Tom Cruise. Cruise plays a green Navy attorney leading the legal team defending two U.S. Marines charged with killing another private, while Nicholson steals the show as the tough and unapologetic Colonel Jessup. 

This Is Spinal Tap

THIS IS SPINAL TAP
Image Credit: Embassy Pictures

This is Spinal Tap walked so that other mockumentaries could run. In fact, Rob Reiner’s directorial debut became the blueprint for many of the fake/satirical documentaries that came after.

The story zooms in on the three ageing members of an English heavy metal band named Spinal Tap, who are struggling to stay relevant in the music industry.

The fact that the film was largely improvised makes it that much more impressive.

The Princess Bride

The Princess Bride
Image Credit: 20th Century Fox

You probably already knew that The Princess Bride would be at the top of the list. This film is one of the best fantasy/adventure/romance/satire/comedies of the 80s and arguably one of the most quotable films in Rob Reiner’s filmography (but that’s largely thanks to William Goldman).

The story takes place in the magical kingdom of Florin, where the beautiful Buttercup (Robin Wright) falls in love with a farmboy named Westley (Cary Elwes). Unfortunately, Westley is believed to be dead after being captured by the Dread Pirate Roberts, and Buttercup is forced to marry the evil Prince Humperdinck. Of course, Westley reemerges to save her from marrying Humperdinck.

Like every great Reiner movie, it’s got witty banter and unforgettable supporting characters. Plus, the grandfather narrating the story helps juggle all the different plot points.

RELATED: Why “You Can’t Handle the Truth” Still Stands as One of Cinema’s Greatest Moments

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About the Author: Caryn Ganess

Caryn Ganess is a South African writer with a sharp eye for sneaker culture and a knack for digging into the psychology behind pop culture. From breaking down the legacy of the Nike Cortez to exploring what makes movie villains tick, she blends academic insight with real-world flavour.

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