Our 10 Rob Reiner Movies

From his first movie to his last, Rob Reiner made movies you can still watch

If you’re from Gen-X, or a lover of film, there is little doubt you have seen most of these. And you can quote them. A lot. Here are some of our favorite Rob Reiner movies. He also had an unusually rare gift for tone. He could pivot from sincere to hilarious, sometimes in the same movie, without undercutting either. He could take a high-concept premise and ground it in character. And he had a knack for creating moments that became cultural shorthand, the kind of lines you hear in real life even from people who have never seen the movie.

This list is not “best in order” so much as “essential Reiner,” the films that show how he built a career on range, warmth, and sharpness. If you’ve only seen one or two, you’re about to have a very good week.

The (Re)Watch Plan

If you want to do this right, pick your lane and build a mini-festival:

The Comfort Triple Feature: The Princess Bride, When Harry Met Sally, The American President
The “I Need to Call My Friends Now and Catch Up” Night: Stand by Me
The Pop Culture Bible Study: This Is Spinal Tap, The Sure Thing
The White-Knuckle Pairing: Misery and A Few Good Men

Reiner’s legacy is not one masterpiece. It’s a shelf of movies people return to when they want to laugh, feel, flirt, or argue with the screen a little. Which is basically the best compliment a director can earn.

Ten Rob Reiner Movies That Define His Legacy As a Director

This Is Spinal Tap (1984)
“These go to eleven.”
Watch it because it basically wrote the rulebook for mockumentary comedy, and the jokes still feel weirdly current.
The core trio is Michael McKean, Christopher Guest, and Harry Shearer as the world’s most confidently delusional band, with Reiner himself as the straight-faced documentarian.
It didn’t just give pop culture a phrase, it gave filmmakers permission to make “real” fake movies and trust the audience to get it.
Stand by Me (1986)
“I never had any friends later on like the ones I had when I was twelve. Jesus, does anyone?”
Watch it because it’s one of the rare coming-of-age films that doesn’t romanticize childhood. It tells the truth about it.
The young cast is stacked: Wil Wheaton, River Phoenix, Corey Feldman, and Jerry O’Connell, with Kiefer Sutherland as a memorably mean presence.
It’s adapted from Stephen King’s novella The Body, and Reiner later said it was the film that “meant the most” to him, which tracks because it feels like he’s directing with his heart out on the table.
The Princess Bride (1987)
“As you wish.”
Watch it because it’s the ultimate “I can’t believe EVERYONE likes this equally” movie: swashbuckling, romance, jokes, sincerity, all of it.
The cast is a miracle, from Cary Elwes and Robin Wright to Mandy Patinkin, André the Giant, Wallace Shawn, and Peter Falk.
It’s also one of those films where the quote culture became the culture, and the sweetness under the comedy is why it never ages out.
When Harry Met Sally… (1989)
“I’ll have what she’s having.”
Watch it because it’s still the smartest argument ever put on screen about love, timing, and the lie we tell ourselves that friendship is “safer.”
Billy Crystal and Meg Ryan are the engine, but the supporting bench (Carrie Fisher, Bruno Kirby) is part of why it feels like real grown-up social life.
It’s widely credited with resetting the standard for modern romantic comedies, and that famous line is delivered by Estelle Reiner, which feels like a Reiner family signature stamped into film history.
Misery (1990)
“I’m your number one fan.”
Watch it for a tight, brutal masterclass in suspense that proves Reiner could pivot from warmth to pure dread without blinking.
James Caan is terrific as the trapped author, but Kathy Bates is the lightning strike, and her performance helped earn her an Oscar win.
It’s also one of the best Stephen King adaptations, partly because it understands that the scariest monster is a human being who thinks they love you.
A Few Good Men (1992)
“You can’t handle the truth!”
Watch it because it’s the rare courtroom movie that plays like a thriller and a character drama at the same time.
It’s an absolute cast flex: Tom Cruise, Demi Moore, Jack Nicholson, Kevin Bacon, Kevin Pollak, Kiefer Sutherland, and more.
If you want a “greatest hits” courtroom drama, AFI literally ranked it among the top courtroom films, and you can feel why as soon as the testimony starts tightening like a noose.
The American President (1995)
“America isn’t easy. America is advanced citizenship.”
Watch it because it’s a political movie that remembers the people inside the suits, and a romance that actually respects intelligence.
Michael Douglas and Annette Bening give it grown-up chemistry, with Martin Sheen and Michael J. Fox rounding out a seriously watchable supporting cast.
Written by Aaron Sorkin, it’s got that muscular, idealistic dialogue that makes you want to argue and believe in the same breath.
The Bucket List (2007)
“We live, we die, and the wheels on the bus go round and round.”
Watch it because it’s a straight shot of movie-star charm with a surprisingly effective emotional punch.
Jack Nicholson and Morgan Freeman are the headliners, and the whole film is built around the pleasure of watching them bounce off each other.
Fun legacy note: the writer’s personal “things to do before I kick the bucket” list is where the phrase “bucket list” came from, and the movie helped turn it into everyday language.
Flipped (2010)
“Some of us get dipped in flat, some in satin, some in gloss, but every once in a while you find someone who’s iridescent, and once you do, nothing will ever compare.”
Watch it because it’s Reiner in full humanist mode: tender, funny, and emotionally accurate about the confusion of first love.
The leads, Madeline Carroll and Callan McAuliffe, are backed by a killer adult cast that includes Rebecca De Mornay, Anthony Edwards, John Mahoney, Penelope Ann Miller, and Aidan Quinn.
It’s based on Wendelin Van Draanen’s novel, and it’s one of those under-sung films that people discover, then immediately text friends like they found a secret.
The Sure Thing (1985)
“I’m not going to bed with you, I’m going to bed in a bed you happen to be in also.”
Watch it because it’s a smart, charming road-romance that understands how attraction is half friction, half timing.
Early John Cusack is in peak form opposite Daphne Zuniga, with a supporting cast that includes Anthony Edwards and Tim Robbins.
It’s also a Christmas break road movie, which gives it that sneaky “holiday hangout” quality, even though it’s really about two people getting over themselves.