Old Hollywood, also known as the Golden Age of Hollywood, was a time when movie stars were more significant than life, and the glitz and glamour of Tinseltown were at their peak. The era lasted from the 1920s to the 1960s, giving rise to some of the most iconic movies and actors ever.
Many filmmakers have paid homage to this period in their work, and numerous films about Old Hollywood are worth watching. The following movies are some of the best movies about Old Hollywood that you should add to your watchlist.

TCM/ IMDb | Sunset Boulevard is noteworthy for being a ruthlessly accurate depiction of the way Hollywood destroys its own legacies
Sunset Boulevard (1950)
Directed by Billy Wilder, "Sunset Boulevard" is a classic movie about the dark side of fame and fortune in Hollywood. The film tells the story of a fading silent film star named Norma Desmond, who hires a struggling screenwriter to help her write a comeback movie.
As their collaboration progresses, the screenwriter realizes that Norma is living in a delusionary world of her own making, where she is still the queen of the silver screen.
Singin' in the Rain (1952)
"Singin' in the Rain" is a musical comedy that takes a lighthearted look at the transition from silent movies to "talkies" in the late 1920s. The film follows the lives of three Hollywood stars, including Don Lockwood (Gene Kelly), who falls in love with a young actress named Kathy Selden (Debbie Reynolds) while trying to make it big in the movie business.
The movie features some of film history's most memorable dance sequences, including the iconic title song.

TCM/ IMDb | The theme song, "The Bad and the Beautiful", penned by David Raksin, became a jazz standard
The Bad and the Beautiful (1952)
"The Bad and the Beautiful" is a gripping drama that tells the story of a ruthless Hollywood producer, Jonathan Shields, who will do whatever it takes to make a successful movie. The film uses flashbacks to explore Shields' relationships with three different people: a director, a screenwriter, and an actress. As the story unfolds, we learn how Shields' ambition and drive have affected their lives.
Mommie Dearest (1981)
"Mommie Dearest" is a biographical drama based on the memoir of Christina Crawford, the adopted daughter of legendary actress Joan Crawford. The film depicts Joan as an abusive and controlling mother who is obsessed with maintaining her public image. Faye Dunaway's performance as Joan Crawford is unforgettable, and the movie is a stark reminder of the dark side of Hollywood.

TCM/ IMDb | "My Week With Marilyn" is based on the true story
My Week with Marilyn (2011)
"My Week with Marilyn" is a biographical drama based on the diary of Colin Clark, who worked as an assistant on the set of the 1957 movie "The Prince and the Showgirl."
The film stars Michelle Williams as Marilyn Monroe, who is shown as a troubled and fragile woman struggling with the pressures of fame. The movie also stars Eddie Redmayne as Colin Clark, who falls in love with Marilyn during their brief encounter.