1. All About Eve (1950)
Written and directed by Joseph L. Mankiewicz (Cleopatra, Julius Caesar), All About Eve follows the titular character Eve Harrington (Anne Baxter) as she is taken under the wing of Broadway legend Margo Channing (Bette Davis). While she first appears to be a young fan, Eve maneuvers her way into Channing’s life, ultimately threatening Channing’s career and personal relationships. Based on the 1946 short story The Wisdom of Eve by Mary Orr, All About Eve was praised by critics at the time of its release, and went on to be nominated for a record 14 Academy Awards. The American drama won six Academy Awards, including Best Picture. All About Eve was also one of the first 50 films to be selected for preservation in the United States Library of Congress’ National Film Registry.
2. Waiting For Guffman (1996)
Waiting For Guffman is an American mockumentary comedy written by Eugene Levy and Christopher Guest, who also serves as the director. As the Missouri town of Blaine approaches its 150th anniversary, eccentric stage director Corky St. Clair (Christopher Guest) casts an eclectic bunch of people including a Dairy Queen worker and an auto mechanic in his show titled “Red White and Blaine.” When St. Clair and the cast of the production learn that a high-profile theater agent is expected to attend opening night, things go overboard. Like other mockumentary films created by Guest, much of the movie’s dialogue is improvised. Additionally, the film contains several original musical numbers written by Guest, Michael McKean, and Harry Shearer.
3. Topsy Turvy (1999)
A British musical film written and directed by Mike Leigh, Topsy-Turvy examines the 15-month long period in 1884 and 1885 leading up to the premiere of The Mikado by lyricist W.S. Gilbert and composer Arthur Sullivan. Topsy Turvy focuses on the dynamic relationship of the famous playwright-composer duo, and their journey to create several more Savoy Operas. Witting and entertaining, the film received praiseworthy reviews and won two Academy Awards, one for Best Costume Design and the other for Best Makeup. Topsy-Turvy is ranked at #481 on Empire’s 2008 list of the 500 greatest films of all time.
4. Stage Fright (1950)
Directed and produced by film household name Alfred Hitchcock, Stage Fright is a British film noir thriller that follows budding actress Eve (Jane Wyman) who tries to help her actor friend (Richard Todd) prove his innocence when he’s accused of murdering the husband of a high-profile entertainer. Playing detective and assuming multiple disguises, Eve later falls into a web of deception and conflict ensues. This film is based on the novel Man Running by Selwyn Jepson, although some changes have been made from the book to the film.
5. Birdman (2014)
This 2014 American black comedy-drama film tells the story of former cinema superhero Riggan Thomson as he struggles to mount a Broadway adaptation of a short story by Raymond Carver. Covering the period of previews up to the play’s opening, Birdman delivers Riggan Thomson’s desire to be portrayed as a true artist and not just a washed-up movie star. Birdman grossed more than $103 million worldwide, and was nominated for a number of Academy Awards in 2015. The film took home Best Picture, Best Director for Alejandro G. Iñárritu, Best Original Screenplay, and Best Cinematography. The film also won the Golden Globe for Best Screenplay and Best Actor in a Motion Picture – Musical or Comedy for Keaton.
6. Noises Off (1992)
Based on the 1982 play of the same name, Noises Off follows director Lloyd Fellowes (Michael Caine) as he is hired to steer the production of an Americanized take on a British play. While things run smoothly during the rehearsal process, chaos ensues as Lloyd and his band of actors begin a series of performances leading up to its Broadway premiere. In his review for the New York Times, Vincent Canby said, “There are a number of hefty laughs scattered throughout . . . this woozy film adaptation.” Directed by Peter Bogdanovich with a screenplay by Marty Kaplan, Noises Off is the comedy where everyone gets caught in the act!
7. Best Worst Thing That Ever Could Have Happened (2016)
Best Worst Thing That Ever Could Have Happened is a 2016 theatrical documentary film that follows the creation of the original Broadway production of Merrily We Roll Along and of the performers that were involved in its making. The documentary is directed by Lonny Price, who is also known for his creation of the role of Charley Kringas in Merrily We Roll Along and for her New York directing work on Sunset Boulevard, Sweeney Todd, and Company. This documentary is available on Netflix for the Broadway addicts and musical lovers in the world.
8. Tootsie (1982)
As the second-most profitable film of 1982, Tootsie remains a major critical and financial success, and an essential for entertainment industry fans everywhere. Directed by Sydney Pollack, Tootsie tells the story of New York actor Michael Dorsey (Dustin Hoffman), who is too hard on himself to the point where his agent cannot find anymore work for him because of his perfectionist mindset. Because he is known to have a reputation for being difficult, he is forced to adopt a new identity as a woman to land a job. What was supposed to be a short-term thing turns into a long-term contract, but Michael falls for his castmate Julie (Jessica Lange), and complications develop from there. The film was nominated for 10 Academy Awards, with Lange winning for Best Supporting Actress. In 1998, the Library of Congress selected Tootsie for preservation in the National Film Registry.
9. Deathtrap (1982)
Based on the 1978 play of the same name by Ira Levin, Deathtrap is an American black comedy mystery that follows Sidney Bruhl (Michael Caine) as he sees his latest Broadway show flop its opening night. The once-successful playwright dives into deep despair until he receives a package from a former student that contains an unproduced script that’s better than anything Sidney has ever written. Sidney comes up with a plan to lure his former student to his home, murder him, and claim the script as his own work. Directed by Sidney Lumet, Deathtrap was given favorable reviews from critics, who also noted its plot similarities to Michael Caine’s 1972 film Sleuth.
10. The Dresser (1983)
The Dresser is a British drama film with a screenplay by Ronald Harwood, based on his 1980 play of the same name. Directed and produced by Peter Yates, The Dresser examines the relationship between an aging Shakespearean actor known as Sir (Albert Finney) and his timid dresser (Tom Courtenay). Formerly a renowned performer, Sir’s work starts to suffer because of his anxiety and age. His efficient and orderly dresser Norman is used to his tirades, and is unfailingly devoted to Sir while struggling to keep his charge’s life together. Tom Courtenay won the Golden Globe Award for Best Actor – Motion Picture Drama. In 2015, the BBC produced a television adaptation of The Dresser starring Ian McKellen and Anthony Hopkins as the leading duo.
11. The Entertainer (1960)
Based on John Osborne’s stage play of the same name, The Entertainer stars Laurence Olivier playing an old-time music hall performer named Archie as his career slowly dies out in the television age. As the music-hall tradition fades, Archie’s personal life also falls apart, with his schoolteacher daughter Jean (Joan Playwright) returns to her hometown at a time of personal crisis, his second wife Phoebe (Brenda De Banzie) being scornful of her husband’s multitude of affairs, and his son Mick (Albert Finney) as a soldier fighting in the Suez. Directed by Tony Richardson, The Entertainer was nominated for an Academy Award for Best Actor in a Leading Role for Olivier.
12. Enter Laughing (1967)
Enter Laughing is a 1967 comedy directed by Carl Reiner, based on his autobiographical novel and stage play of the same name. Being Reiner’s directorial debut, Enter Laughing follows David Kolowitz (Reni Santoni) as he dives into his pursuit of an acting career during the Great Depression, despite the opposition of his parents and girlfriend. He manages to land a non-paying role in an Off-Broadway show under the direction of Harrison B. Marlowe. Despite his lack of experience, David continues to chase his aspirations to get into show business.
13. To Be Or Not to Be (1942 & 1983)
To Be Or Not to Be follows acting couple Joseph and Maria Tura as they lead a troupe of actors when Nazis invade Poland during World War II. This acting troupe use their abilities at disguise and acting to fool the occupying troops. The 1942 film was directed by Ernst Lubitsch and stars Carole Lombard and Jack Benny as Maria and Joseph, respectively. In 1996, this film was selected for preservation in the United States National Film Registry by the Library of Congress. The film was remade in 1983, which starred Mel Brooks and Anne Bancroft as the lead couple. The 1983 remake was mostly faithful to the 1942 film, and dialogue was taken verbatim from the previous film.
14. Shakespeare in Love (1998)
Directed by John Madden and written by Marc Norman and playwright Tom Stoppard, Shakespeare in Love tells the story of an imaginary love affair between William Shakespeare (Joseph Fienne) and Viola de Lesseps (Gwyneth Paltrow) at the time when Shakespeare was writing Romeo and Juliet. Several characters in the film are based on historical figures, and there are many allusions to Shakespearean plays throughout the film as well. It was a box office success and received positive reviews from critics, making it the ninth-grossing film of 1998. Shakespeare in Love took home 7 Academy Awards, including Best Picture, Best Actress for Paltrow, Best Supporting Actress for Judi Dench, and Best Original Screenplay.
15. Opening Night (1977)
Written and directed by John Cassavetes, Opening Night follows actress Myrtle Gordon (Gena Rowlands) who is awaiting the anticipated release of Second Woman, in which she portrays a woman distraught about aging. One night Myrtle signs autographs and encounters an obsessive young fan, who is later killed by a car when chasing Myrtle’s limousine. Throughout the film, Myrtle struggles to connect to the character she is playing, and her state of mind deteriorates as she continues to have visions of the teenage fan, which Myrtle considers as a projection of her youth. As she gets closer to opening night, Myrtle tries to find a way to make the show go on.
16. Last Summer in the Hamptons (1995)
Directed by Henry Jaglom, Last Summer in the Hamptons is a comedy-drama that revolves around a family of theatrical actors, playwrights, and directors spending their last summer together in the Hamptons. This last summer is due to the matriarch Helena Mora’s (Viveca Lindfors) decision to sell her Hamptons home because of financial troubles. However, bringing together a family full of people in the show business creates tension, especially when Oona (Victoria Foyt) seeks the approval of her creative peers as she aspires to start a theatre career after desiring to leave Hollywood.
17. Synecdoche, New York (2008)
Starring Philip Seymour Hoffman, Synecdoche is Charlie Kaufman’s directorial debut that follows theatre director Caden Cotard as he creates a life-size replica of New York City inside a warehouse for his latest play. His desire to create an intricately-detailed production stems from his troubling personal life; his wife and daughter have left him and he also suffers from numerous physical ailments. After receiving a MacArthur Fellowship that gives him the financial means to explore his artistic interests, Caden is determined to craft a piece of realism and honesty, which begins to blur the boundaries between fiction and reality. Synecdoche, New York appeared on many critics’ top ten-list of the best films of 2008, and was also nominated for the Palme d’Or at the 2008 Cannes Film Festival.
18. Pygmalion (1938)
Based on the George Bernard Shaw play of the same name, Pygmalion follows linguistic professor Henry Higgins (Leslie Howard) as he trains Cockney flower girl Eliza Doolittle (Wendy Hiller) as a princess within a six-month timespan. After Higgins makes a financial agreement with her dustman father, Eliza moves into Higgins’ home and begins her training and transformation into British high-class society. The film was a financial and critical success, winning Best Screenplay at the Oscars. The screenplay was later adapted into the 1956 musical My Fair Lady, which led to the 1964 film of the same name starring Audrey Hepburn and Rex Harrison as Eliza Doolittle and Henry Higgins, respectively.