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10 Modern Movies to Watch if You Adore Classic Hollywood

If you miss classic Hollywood, these movies are for you.

Today’s audiences love contemporary movies that highlight the classic Hollywood era. Be it the fondness for definitive Hollywood glamour, style, or innocence, these movies evoke feelings of nostalgia and a longing for what appeared to be a simpler time.

Whether it is Mank‘s well-crafted and timeless storytelling or the chance to discover the darker underside of the alluring Hollywood in Babylon, these modern movies resonate with audiences.

10. ‘Hail, Caesar!’ (2016)

Hail, Caesar

Eddie Mannix (Josh Brolin) is the head of the production at Capitol Pictures and is attempting to solve all the issues the actors and filmmakers have in the movie Hail Caesar! Mannix meets his biggest challenge when Baird Whitlock (George Clooney) gets abducted and needs rescuing.

Set in the 1950s, Hail, Caesar! illustrates different film genres of the time, such as musicals, Westerns, and epics. It also references real-life Hollywood figures such as real-life fixer in Hollywood during the Golden Age Mannix. Through its reflective and comedic portrayal of classic Hollywood, Hail, Caesar! emphasizes the glitz and glamour, as well as the challenges and controversies of the time.

9. ‘The Artist’ (2011)

The Artist (2011) (1)

In the movie The Artist, actor George Valentine (Jean Dujardin) is a superstar actor in the 1920s. While working on his latest film, Valentin falls in love with a young aspiring actress named Peppy Miller (Bérénice Bejo); however, as the popularity of sound in movies rises, it further divides their relationship.

The Artist is a love letter to the Golden Age of Hollywood, capturing this iconic era’s look, feel, and spirit. It pays homage, specifically to the late 1920s to the early 1930s, with its black-and-white cinematography and use of light and shadow, creating a wistful atmosphere that evokes the era. The movie also mirrors the real-life challenges that many actors and filmmakers faced during the transition from silent to sound film.

8. ‘La La Land’ (2016)

Emma Stone and Ryan Gosling in 'La La Land'
Image via Lionsgate

Sebastian Wilder (Ryan Gosling) and Mia Dolan (Emma Stone) meet and start a relationship while pursuing their dreams and struggling to make ends meet in the movie La La Land. As the two become more successful, their relationship begins to fall apart.

La La Land incorporates the Golden Age of Hollywood with its tribute to the 1950s and 1960s musical eras. The film’s original songs and dance numbers reflect the jazz-infused musicals of this era, and its choreography is reminiscent of classic Hollywood dance numbers. Not to mention the film’s production design and cinematography feature splashy colors, and exquisite sets, absorbing the audience into the world of classic Hollywood.

7. ‘Ed Wood’ (1994)

Johnny Depp in Ed Wood

Director Ed Wood (Johnny Depp) is a Hollywood pariah due to his unorthodox and bizarre filmmaking practices in the Tim Burton movie Ed Wood. However, with the support of Bela Lugosi (Martin Landau) and a loyal cast and crew, Wood produces a strangely captivating series of seriously low-budget films.

While the movie Ed Wood may not be a straightforward tribute to classic Hollywood, the film delivers a peek into the world of low-budget filmmaking in 1950s Hollywood and the challenges faced by filmmakers. The visual of the artistically stylized sets and costumes and the depiction of a B-movie director who worked outside the mainstream Hollywood system offer the audience a different perspective of the classic age.

6. ‘Once Upon a Time In Hollywood’ (2019)

Two guys are leaning against the wall and posing for the picture

Written and directed by Quentin Tarantino, the movie Once Upon a Time in Hollywood follows actor Rick Dalton (Leonardo DiCaprio), a former 1950s television Western, now struggling to find work. Dalton spends most of his days partying with Cliff Booth (Brad Pitt) but ultimately finds himself entangled with the members of the Manson Family.

Once Upon a Time in Hollywood captures the look, feel, and spirit of this iconic era in Hollywood history while also probing into the folklore and legends that have evolved into a vital part of the industry’s legacy. The film supplies a window into the world of Hollywood in the late 1960s when the industry was undergoing significant changes and scandals were prominent.

5. ‘The Aviator’ (2004)

The Aviator

Howard Hughes (Leonardo DiCaprio) is a thriving billionaire and aviation mogul who directed big-budget Hollywood films during the 1930s in the movie The Aviator. While Hughes helped build TWA into a major airline, he also remained troubled, suffering from overwhelming phobias and depression.

Not only does the movie The Aviator ingeniously captures the look, feel, and spirit of this iconic era in Hollywood history, but it also examines the life and legend of one of its most enigmatic figures. The film features several actors who are known for their work in classic Hollywood films, including Katherine Hepburn (Cate Blanchett), a legendary Hollywood actress. Plus, the history of Hughes’s life offers a reinvigorated view of this intriguing aspect of Hollywood history.

4. ‘L.A. Confidential’ (1997)

L.A. Confidential (1997)

L.A. Confidential reveals the story of Detective Lieutenant Exley (Guy Pearce), Officer White (Russell Crowe), and Sergeant Vincennes (Kevin Spacey) as they venture to expose the corruption surrounding an unsolved murder at a downtown Los Angeles coffee shop in the early 1950s. The movie was nominated for nine Academy Awards and was a critical and commercial success.

This neo-noir crime film skillfully captures the spirit and essence of this era. From the vintage cars to the classic Hollywood-style orchestral score, audiences are immersed in the nostalgic atmosphere of classic Hollywood while still taking a stroll down the darker side of the entertainment industry and the city of Los Angeles.

3. ‘Mank’ (2020)

Mank

The 2020 black-and-white biographical drama film, Mank, follows alcoholic screenwriter Herman J. Mankiewicz (Gary Oldman) as he races to finish the movie Citizen Kane. Producer and director Orson Welles (Tom Burke) arranges for Mankiewicz to live in a house near the desert, supplying him with cigarettes, alcohol, and a typist named Rita (Lily Collins) but expects the script in 60 days.

Mank underscores the life and legend of one of the most influential screenwriters of the Golden Age of Hollywood. Mankiewicz was a powerful player in Hollywood in the 1930s and 1940s. The movie offers a fresh viewpoint on this intriguing part of Hollywood history. One of the highest-paid screenwriters of the time, Mankiewicz struggled later in his career after years of heavy drinking and gambling. The movie is gritty and honest, with an all-too-truthful view of classic Hollywood.

2. ‘Hollywoodland’ (2006)

Ben Affleck sitting next to Diane Lane in a crowd of people holding hands in Hollywoodland

While investigating the mysterious death of Superman actor George Reeves (Ben Affleck) in 1959, detective Louis Simo (Adrien Brody) uncovers a link to his life in the movie Hollywoodland. Simo soon learns about an affair that Toni Mannix (Diane Lane), who was in a romantic relationship with Reeves and was the wife of MGM studio executive Eddie Mannix (Bob Hoskins), might be the key to cracking the case.

Hollywoodland production design and cinematography seamlessly reflect the demeanor and ambiance of Hollywood films from the 1950s. The movie also shines a light on the challenging and sinister side of classic Hollywood, including its scandals, corruption, and crime.

1. ‘Babylon’ (2022)

Brad Pitt as Jack Conrad on a poster for Babylon
Image via Paramount Pictures

Babylon recounts the corruption, debauchery, and absurd excess in classic Hollywood that lead to the collapse of many ambitious entertainers in the 1920s, including Jack Conrad (Brad Pitt) and Nellie LaRoy (Margot Robbie). As Hollywood shifted from silent pictures to the world of sound films, stars needed to find a way to adapt or become obsolete.

Babylon energetically explores the not-so-glamour side of Hollywood’s Golden Age. Set in the 20s and 30s, the movie underscores how that period provided an exhausting amount of success and failure, change, and upheaval in Hollywood. Babylon shows a view of Hollywood as not only a place and an idealized belief.

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