The 10 Best Movies About Classic Hollywood, Ranked

The Golden Age of Hollywood is one of the most beloved eras of all time, especially by die-hard cinephiles. As such, it is only natural that it has been replicated one too many times on the big screen, with audience members fully immersing themselves in its glamour and elegance. In fact, this happens quite so often that it almost feels like Hollywood is in its era of making movies about making movies.

With that being said, the appeal of the long-lost era of great movie stars, as some say, is undeniable. As such, we gathered 10 of the best movies about classic Hollywood, from Chaplin to Sunset Boulevard, that will make audiences feel like they're, too, a part of the Golden Age.

10 'Chaplin' (1992)

Director: Richard Attenborough

Featuring Robert Downey Jr. in a career-defining performance that earned him a Best Actor nomination (though his Oscar-winning role in last year's Oppenheimer arguably comes close), Richard Attenborough's biopic Chaplin brings comedy and drama together, as expected, by illustrating an elderly Chaplin as he discusses his autobiography with his editor and recounts his once-in-a-lifetime journey, from his poor childhood to worldwide success.

Despite receiving mixed reviews (and underperforming at the box office), Downey's performance in Chaplin makes it worthwhile. Needless to say, Attenborough's movie about the iconic English actor is a must-see for Chaplin enthusiasts. While by no means a masterpiece, Chaplin is still an engaging viewing experience that provides viewers with insight into the life of the legendary star while shedding light on themes of class and wealth.

Chaplin

Watch on Amazon Prime

9 'Babylon' (2022)

Director: Damien Chazelle

When the subject is polarizing films, Babylon is an obvious mention. The epic Damien Chazelle feature released in 2022 stars Margot Robbie in one of her most memorable roles and depicts the rise and fall of multiple characters — including Robbie's aspiring movie star Nellie Laroy, who was heavily based on Clara Bow much like other characters in the film were based on real-life people — during Hollywood's transition from silent to the "talkies" in the late 1920s.

If audiences are on the lookout for modern movies about Hollywood's golden age, Babylon may be the right pick despite its mixed reviews. While some argue that it is a bit too ambitious for its own good, others believe that Chazelle's visual feast is one of the most unfairly underrated movies of 2022. Be that as it may, Babylon is surely unique and probably unlike anything audiences have ever seen.

Babylon

Watch on Amazon Prime

8 'L.A. Confidential' (1997)

Director: Curtis Hanson

Directed by Curtis Hanson and based on James Ellroy's 1990 novel of the same name (the third book in his L.A. Quartet series), L.A. Confidential is an engaging film that tackles corruption as it takes viewers back to the 1950s. The story follows three policemen (RussellCrowe, GuyPearce, and KevinSpacey) as they investigate a string of murders, each with their own motives and brand of justice.

Featuring an impressive 99% Rotten Tomatoes score, Hanson's crime drama is a must-see in this niche genre, making for an incredible watch in the crime and detective categories as well. In addition to its smart, sharply written, and well-paced narrative that highlights redemption and justice, the beautifully shot neo-noir also benefits from impressive camerawork and great acting performances.

L.A. Confidential

Watch on Hulu

7 'Barton Fink' (1991)

Directors: The Coen Brothers

Although the Coens' Hail Ceasar! could also make it to this list, Barton Fink is arguably the filmmaker's best effort when it comes to films that celebrate classic Hollywood. Featuring a younger John Turturro in the lead role, this dark comedy and psychological thriller set in the 1940s follows a young New York City playwright who is hired to write scripts for a film studio in Hollywood.

Nominated for three Academy Awards in spite of being an obvious box office bomb (and an underrated feature by the talented duo), this great 21st-century whodunit is still well worth the watch; Barton Fink is the ideal pick for those who like writing and the writing process as much as they love the Golden Age of Hollywood. Furthermore, this Coen Brothers movie elucidates the conditions of labor in creative industries.

Barton Fink

Rent on Apple TV

6 'The Artist' (2011)

Director: Michel Hazanavicius

Starring JeanDujardin and BéréniceBejo in the lead roles, the black-and-white The Artist is one of 2011's finest. The story revolves around a silent movie superstar who meets dancer Peppy Miller with sparks quickly flying between the two. However, their dynamics and fortunes are affected during the transitioning era of classic Hollywood, with the introduction of talking movies.

Michel Hazanavicius' high-rated movie is essential viewing regarding features about Hollywood's Golden Age because it pays a wonderful homage to that particular era, particularly noting how difficult it was for some silent actors to carry on doing what they loved while seeing others succeed. Made with no sound and shot in the old 4:3 ratio, The Artist is a unique achievement by Hazanavicius that sends audiences back to such a special, defining moment in time for cinema.

The Artist

Watch on Amazon Prime

5 'The Bad and the Beautiful' (1951)

Director: Vincente Minnelli

One of the oldies but goldies that depicts the film industry during the classic era is The Bad and the Beautiful, a Vincente Minnelli picture that stars Kirk Douglas and Lana Turner. It centers around a movie producer who uses (and manipulates) an actress, a director (BarrySullivan), and a writer (DickPowell) in order to toil his way to the top of the studio system.

This entertaining but underrated Golden Age melodrama should be on the watchlist of every classic Hollywood enthusiast. With six Academy Award nominations, The Bad and the Beautiful broke a record for the most awards for a movie that was not nominated for Best Picture or Best Director the following year after it was released and was very well-received by both audiences and critics alike. While not on the same level as other films mentioned next, Minnelli's efforts are certainly worth the while, especially in how the filmmaker satirizes the egos that shape the film industry.

Rent on Apple TV

4 'Sullivan's Travels' (1941)

Director: Preston Sturges

Centering around Joel McCrea's naive but good-natured Hollywood director John L. Sullivan, Preston Sturges' Sullivan Travels illustrates Sullivan's journey to experience life as a homeless person to gain relevant life experience for his next big project, as he aspires to make a film about the troubles of the oppressed and subjugated poor.

Often taking a spot in the best movies of the 1940s lists ever since it came out, with its reputation increasingly improving, Sturges' black-and-white picture starring the iconic, talented bombshell Veronica Lake is an undeniably empathetic tale that deals with universal themes such as suffering, kindness, and generosity. For audiences who are looking to watch a heartfelt classic movie that celebrates the industry, Sullivan Travels may be the right choice.

Rent on Apple TV

3 'A Star is Born' (1954)

Director: George Cukor

One of the most famous and celebrated takes on the famous RobertCarson, DorothyParker and AlanCampbell screenplay of the same name is the Judy Garland-led 1954 film. The story focuses on a movie star who helps a young singer and actress make her way to fame and achieve her dreams. In the meantime, Norman Main struggles with age and alcoholism, which ultimately sends his career on a downward spiral.

Although the Bradley Cooper and Lady Gaga movie of the same name is a fan-favorite, George Cukor's film is undoubtedly at the top of the adaptation list (fun fact: it is also the longest of the bunch and the first take of the tale that focuses on musicians). There are many reasons why this 1954 epic endures an incredible watch today and why it may appeal to anyone interested in films about classic Hollywood. Its astounding performances, for one, are worth mentioning: Garland is at her career-best in this timeless, Academy Award-nominated feature.

Watch on Tubi

2 'Singin' in the Rain' (1952)

Directors: Stanley Donen, Gene Kelly

Regarded as one of the best movies of all time, Singin' in the Rain had to take a spot on this list — after all, the Gene Kelly-led feature directed and choreographed by Kelly and StanleyDonen is iconic for a reason. Its plot revolves around a silent film star who falls for a chorus girl (DebbieReynolds) as he and his screen partner (Donald O'Connor) attempt to make the difficult transition to talking pictures in 1920s Hollywood.

One of the first 25 films selected by the United States Library of Congress for preservation in the National Film Registry, the 1952 classic by Donen and Kelly is understandably essential viewing to anyone who is into Hollywood's Golden Age or musicals (or both). Although the unforgettable, likable characters are part of what makes it so good, Singin' in the Rain benefits greatly from its dance sequences and musical numbers.

Singin in the Rain

Watch on Max

1 'Sunset Boulevard' (1950)

Director: Billy Wilder

At last, Sunset Boulevard takes home the crown for the best movie about classic Hollywood, as it perfectly captures the essence of the often glamorized era, shedding light on self-deceit, fame, greed, and narcissism through its enjoyable narrative. It follows struggling screenwriter Joe Gillis (William Holden) and former silent film star Norma Desmond (GloriaSwanson), who draws him into her fantasy world where she dreams of making a triumphant comeback to the screen.

Sunset Boulevard is certainly the best movie about movies out there so far, with many critics regarding it as a true masterpiece of American cinema. The elements that get Sunset Boulevard the most praise are the incredible acting efforts, the film-noir atmosphere, and its cynical mood that makes it work incredibly well as a sharp, biting satire.

Sunset Boulevard

Watch on Hoopla

NEXT: The 15 Best Classic Romance Movies of Hollywood’s Golden Age

ncG1vNJzZmibn6G5qrDEq2Wcp51kurDCyJ6qZpmSpMK1ec6lm2agn6G5usPOqJtmqpGjuKawjg%3D%3D