10 Most Rewatchable Old Hollywood Movies That Still Hold Up

Old Hollywood is associated with glamour and romance, and many of the great classics of the era are still worth watching in the 21st century. Also referred to as the Golden Age of Hollywood, Old Hollywood was classified by the studio system, which signed big-name movie stars and directors to multi-movie contracts. There’s some debate over when exactly it ended, but New Hollywood emerged at some point during the 1960s.

Since the apogee of Old Hollywood took place from the 1930s to 1950s, it’s only natural that some of the era’s greatest movies don’t hold up so well today. Modern audiences have different tastes, but there are still plenty of classics which are just as enjoyable. Movies like Casablanca, Bringing Up Baby and North By Northwest have stood the test of time, and they are still being watched by people all over the world.

10

Casablanca (1942)

Bogart And Bergman Are Irresistible Together

Casablanca Movie Poster

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8.7/10

Casablanca

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Release Date

January 23, 1943

Director

Michael Curtiz

Cast

Humphrey Bogart
, Ingrid Bergman
, Paul Henreid
, Claude Rains
, Conrad Veidt
, Sydney Greenstreet

Casablanca has stood the test of time, and it’s now considered one of the best romance movies ever made. Humphrey Bogart and Ingrid Bergman were two of the biggest stars in Hollywood at the time, and they are both on top form in Casablanca. Their chemistry is part of what makes the romance so realistic and ultimately heartbreaking, but they also benefit from an outstanding script and a great supporting cast.

Casablanca has stood the test of time, and it’s now considered one of the best romance movies ever made.

Casablanca is one of the most quotable movies ever, and it’s always a joy to go back and watch Bogart’s jaded, hangdog expressions as he grabs hold of each line. The tearjerker of an ending is the final cherry on top which cements Casablanca‘s iconic status. Even without its Second World War context, Casablanca is a timeless story about the cost of love and freedom that still rings true.

9

North By Northwest (1959)

Hitchcock’s Thriller Has Influenced Countless Spy Dramas

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North By Northwest

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Release Date

September 8, 1959

Director

Alfred Hitchcock

Cast

Eva Marie Saint
, James Mason
, Cary Grant
, Leo G. Carroll
, Jessie Royce Landis

Three years before Dr. No kicked off the James Bond franchise, Alfred Hitchcock delivered one of the best espionage thrillers ever made. The style of Bond and many other spy movies owe a great debt to North By Northwest. The helicopter scene in From Russia With Love may be the franchise’s most obvious reference to North By Northwest, but the tone and the big-screen characterization of Bond also seem to take inspiration from Hitchcock.

The style of Bond and many other spy movies owe a great debt to North By Northwest.

Many of Alfred Hitchcock’s best movies are still just as enjoyable many decades later. Psycho, Vertigo, Rear Window and Dial M for Murder – to name just a handful – still pack a punch. There aren’t many Golden Age directors who still have such a sizable audience in the 21st century. North By Northwest is one of his most entertaining movies, barreling from one action scene to another, while still providing some moments to allow Cary Grant and Eva Marie Saint’s chemistry to flourish.

8

12 Angry Men (1957)

12 Angry Men Still Sets The Standard For Legal Dramas

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12 Angry Men

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Release Date

April 10, 1957

Director

Sidney Lumet

Cast

John Fiedler
, Henry Fonda
, Martin Balsam
, Jack Klugman
, Lee J. Cobb
, E.G. Marshall

12 Angry Men looks and feels like a stage play, but it was developed as a movie based on a teleplay. The close confines of 12 Angry Men‘s single location never feel too restrictive. In fact, the deliberation room is the perfect pressure-cooker environment as a dozen men from different walks of life lock into a battle of wills. Sidney Lumet constantly finds new and inventive ways of framing his characters.

The 12 Angry Men movie jurors at the table.

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12 Angry Men is a masterpiece of conflict and dialogue, with a very limited concept that reduces all outside distractions. It’s the kind of movie that could and should be studied in detail, so every rewatch reveals new details about the characters. Also, 12 Angry Men‘s ending doesn’t solve the mystery at hand. It merely offers a verdict on the trial, but there are a lot of unanswered questions and potential errors in the jury’s process.

7

The Treasure Of The Sierra Madre (1948)

The Treasure of the Sierra Madre Movie Poster

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The Treasure of the Sierra Madre

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Release Date

January 24, 1948

Director

John Huston

Cast

Humphrey Bogart
, Walter Huston
, Tim Holt
, Bruce Bennett
, Barton MacLane

The Treasure of the Sierra Madre is Humphrey Bogart’s best western, and one of the best westerns of all time. Bogart stars alongside Tim Holt and Walter Huston – the director’s father – as a trio of prospectors who find their fortune in a gold deposit in Mexico, but this turns out to be a false dawn. The Treasure of the Sierra Madre is a brilliantly written and acted exploration into greed and paranoia.

Bogart was robbed of an Oscar nomination for The Treasure of the Sierra Madre. It’s one of his most captivating performances, and his character inspired Breaking Bad‘s Walter White and There Will Be Blood‘s Daniel Plainview. He brews a potent mixture of greed and jealousy that heightens the impact of the script. It’s a tense exploration into human nature, but it can also be seen as an allegory for America’s westward expansion.

6

Singin’ In The Rain (1952)

Singin’ In The Rain Is A Landmark Musical

Singin' in the rain movie poster

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Singin’ in the Rain

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Release Date

April 11, 1952

Director

Stanley Donen
, Gene Kelly

Cast

Gene Kelly
, Donald O’Connor
, Debbie Reynolds
, Jean Hagen
, Millard Mitchell
, Cyd Charisse

Singin’ In The Rain epitomizes the lavish style of Old Hollywood musical movies. It’s a feast for the eyes, from the set design to the choreography, and it has only gotten better with age as its particular style of musical has become vanishingly rare. The 1950s and 1960s produced several Best Picture-winning musicals. Singin’ In The Rain wasn’t one of them, but it’s just as entertaining as The Sound of Music, West Side Story or Gene Kelly’s 1951 winner An American In Paris.

Singin’ In The Rain epitomizes the lavish style of Old Hollywood musical movies.

Gene Kelly is a delight throughout Singin’ In The Rain, and many of his co-stars get their own moments to shine – like Donald O’Connor’s unforgettable solo number, “Make ‘Em Laugh”. Singin’ In The Rain is all about Hollywood’s transition from silent films to talkies, and its period setting means that it has aged brilliantly. It’s a love letter to the medium of film itself, with wonderful exuberance and commitment to entertainment.

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5

The Wizard Of Oz (1939)

The Wizard Of Oz Remains A Defining Work Of The Fantasy Genre

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20

8.6/10

The Wizard of Oz

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Release Date

August 25, 1939

Director

Victor Fleming

Cast

Margaret Hamilton
, Jack Haley
, Judy Garland
, Bert Lahr
, Ray Bolger

Back in 1939, The Wizard of Oz was praised for its marvelous technicolor artistry. It’s remarkable that it still has the power to immobilize and captivate audiences so many decades later. The transition from the dreary sepia of Dorothy’s home to the rainbow wonderland of Oz sums up the allure of The Wizard of Oz. In some ways, it also sums up the magic of the entire fantasy genre.

The transition from the dreary sepia of Dorothy’s home to the rainbow wonderland of Oz sums up the allure of The Wizard of Oz.

Thanks to the success of Wicked, The Wizard of Oz is once again back in the cultural zeitgeist, with audiences discovering and rediscovering its charms. It looks more inviting and exciting than most movies which are being made today, but it also tells an endearing story of friendship and family. The core character archetypes of The Wizard of Oz have been copied and reinterpreted in countless ways, but the original movie still has its power.

4

Roman Holiday (1953)

An Enduring Romance With Breezy Charms

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Roman Holiday

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Release Date

August 26, 1953

Director

William Wyler

Cast

Audrey Hepburn
, Gregory Peck
, Eddie Albert
, Hartley Power
, Harcourt Williams
, Margaret Rawlings
, Tullio Carminati
, Paolo Carlini
, Claudio Ermelli
, Paola Borboni
, Alfredo Rizzo
, Laura Solari
, Gorella Gori
, Armando Annuale
, Maurizio Arena
, Gildo Bocci
, Andrea Esterhazy
, George Higgins
, Richard McNamara
, Luigi Moneta
, Piero Pastore
, Mimmo Poli
, Giuliano Raffaelli
, Carlo Rizzo
, Gianna Segale

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Roman Holiday is one of Audrey Hepburn’s best movies, and it secured her the Oscar for Best Actress. It has lost none of its appeal over the years, thanks to the infectious charisma of Hepburn and her co-star Gregory Peck. Roman Holiday feels like the kind of weighty romance that studios rarely make these days. There are plenty of laughs, but it’s also a gut-wrenching story of insurmountable odds and missed chances.

Roman Holiday feels like the kind of weighty romance that studios rarely make these days.

Roman Holiday is light on its feet, as the two main characters explore a beautiful city together with a natural flow to their conversation and every stolen glance. It’s a film worth getting wrapped up in, and there’s a catharsis to the heartbreaking ending. Not everyone can relate to the story of a princess escaping her entourage, but anyone can identify with the joy and the agony of her adventure.

3

Bringing Up Baby (1938)

Arguably The Funniest Screwball Comedy Ever

Bringing Up Baby Official Poster

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Bringing Up Baby

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Release Date

February 18, 1938

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Director

Howard Hawks

Cast

Katharine Hepburn
, Cary Grant
, Walter Catlett
, Barry Fitzgerald

It’s hard to believe that Bringing Up Baby was Katharine Hepburn’s first comedy movie, since she is a force of nature as the fast-talking, flighty socialite Susan Vance. She and Cary Grant are the perfect odd couple, with him as the awkward, nervous paleontologist who gets dragged across the country with a leopard in the back seat of the car. It’s a ludicrous comedy that hits all the right notes, and it makes the most of its wild premise.

Cary Grant’s David is the only character who listens or thinks more than he talks. Throughout Bringing Up Baby, characters use language to deceive, to fill time and to cause a scene, but they rarely use it to communicate any useful information. The comedy is built around a series of uproarious misunderstandings and flat-out lies, as well as a healthy dose of slapstick. It’s so quick-witted and densely packed that it always has something to offer on a rewatch.

2

Citizen Kane (1941)

Orson Welles’ Masterpiece Deserves Its Reputation

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Citizen Kane

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Release Date

April 17, 1941

Director

Orson Welles

Cast

Orson Welles
, Joseph Cotten
, Dorothy Comingore
, Agnes Moorehead
, Ruth Warrick
, Ray Collins

Over the years, the name Citizen Kane has been synonymous with towering, imposing works of art. For example, when actors and filmmakers want to be self-effacing about a certain project, they might say that they aren’t trying to make Citizen Kane. This makes the movie seem far less accessible than it really is. In truth, Citizen Kane is endlessly entertaining, easy to get into, and even surprisingly funny in places.

A collection of characters from the greatest movies of all time including Woody the Cowboy from Toy Story, the Godfather, and Frodo Baggins

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14

Orson Welles’ directorial debut tracks the life of a newspaper magnate through his triumphs and failures. The story is set in motion by the investigation into his enigmatic final words, but it soon becomes an in-depth character study that ties into the hollow promise of the American dream. Citizen Kane mixes its intelligent thematic explorations with sheer entertainment value. Audiences shouldn’t be put off by its highbrow reputation.

1

The Killing (1956)

Stanley Kubrick’s Heist Classic Is Short But Sweet

The Killing 1956

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The Killing

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Release Date

June 6, 1956

Director

Stanley Kubrick

Cast

Sterling Hayden
, Coleen Gray
, Vince Edwards
, Jay C. Flippen
, Ted de Corsia
, Marie Windsor
, Elisha Cook Jr.
, Joe Sawyer

Stanley Kubrick eventually became an icon of New Hollywood, but his earlier movies show glimmers of his genius while he was still working within the confines of the Old Hollywood studio system. The Killing is a thrill ride coming in at less than 90 minutes, but it still offers a lot to love. Sterling Hayden plays the leader of a group of thieves who aim to knock off a racetrack and split the loot.

The Killing is a thrill ride coming in at less than 90 minutes, but it still offers a lot to love.

Along with Jules Dassin’s Rififi, The Killing helped to establish the conventions of the heist genre, and its influence can still be seen in the 21st century. As with many great heist movies, there’s a gulf between the plan and the execution in The Killing. With a dash of humor and some frantic action, The Killing holds up to multiple watches. It may not be as ambitious as Kubrick’s later works, but it’s well worth watching.

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