Match the Best Actress Oscar Winners - 1920s/30s Quiz

Answer: Janet Gaynor

Janet Gaynor picked up the very first Academy Award for Best Actress at the first ceremony which was held in 1929 to recognize films from 1927 and 1928. At that ceremony, performers could be nominated for their work in multiple films, and Gaynor received the award for the films "7th Heaven" and "Sunrise: A Song of Two Humans" from 1927, and "Street Angel" from 1928, all silent films.

In "7th Heaven", Gaynor fell in love with a street cleaner (Charles Farrell) who saved her life as WWI began. In "Sunrise: A Song of Two Humans", Gaynor portrayed the wife of an unfaithful man (George O'Brien) who tried to kill her but had second thoughts.

In "Street Angel", Gaynor portrayed a prostitute who had escaped from the police and hidden in a circus where she met and fell for an artist (Charles Farrell) who was unaware of her past.

The other contenders for the first Best Actress award were Louise Dresser ("A Ship Comes In") and Gloria Swanson ("Sadie Thompson"), both silent film performances.

Answer: Mary Pickford

"America's Sweetheart" Mary Pickford won the only competitive Oscar of her career for her role as Southern belle Norma Besant in "Coquette". The film was the first "talkie" for the Canadian silent film star, and she campaigned for the award, reportedly inviting the judges to tea at her Pickfair home.

In "Coquette", the flirtatious Besant wanted to marry a local bad-boy (Johnny Mack Brown) against the wishes of her father (John St. Polis), but after her reputation was damaged, her father killed the man, and she was forced between protecting him or telling the truth.

The other contenders for Best Actress were Ruth Chatterton ("Madame X"), Betty Compson ("The Barker"), Corinne Griffith ("The Divine Lady"), Bessie Love ("The Broadway Melody"), and Jeanne Eagels ("The Letter"). Eagels received the first posthumous Academy Award nomination, having died sixth months after her film had been released. All of the performances were in talkies with the exception of "The Barker" which was considered a part-talkie with some sound sequences and "The Divine Lady" which had sound effects and music but no spoken dialogue.

Answer: Norma Shearer

Norma Shearer received two Best Actress nominations at the third Academy Awards ceremony, and she took home the Oscar for her role as Jerry Martin in "The Divorcee". Her other nomination was for "Their Own Desire". At the ceremony, Shearer's brother Douglas Shearer won the Oscar for Best Sound Recording, making them the first sibling Oscar winners.

In the pre-Code "The Divorcee", Martin was a party girl who divorced her philandering husband (after having an affair 'to even the score') only to reevaluate her life after returning to her partying ways.

The other nominees were Nancy Carroll ("The Devil's Holiday"), Ruth Chatterton ("Sarah and Son"), Greta Garbo ("Anna Christie" and "Romance"), and Gloria Swanson ("The Trespasser").

Answer: Marie Dressler

Marie Dressler won the Best Actress Oscar for her role as streetwise innkeeper Min Divot in "Min and Bill". At the ceremony, Dressler was sitting next to nine-year-old Jackie Cooper, who had snagged a Best Actor nomination for the film "Skippy", and Mr. Cooper had fallen asleep against her.

When her name was called as the winner, Cooper had to be gently moved aside. In "Min and Bill", Min was raising the abandoned daughter of a prostitute and trying to keep her sheltered from the rough ways of the docks where the inn was located. Fisherman Bill (Wallace Beery) was Min's drinking and sparring partner.

The other nominees for the Best Actress award were Marlene Dietrich ("Morocco"), Irene Dunne ("Cimarron"), Ann Harding ("Holiday"), and Norma Shearer ("A Free Soul").

Answer: Helen Hayes

At the fifth Academy Awards ceremony, Helen Hayes won the Oscar for Best Actress for her role as disgraced woman Madelon Claudet in "The Sin of Madelon Claudet". Although Hayes had appeared in a few silent roles, the performance was largely considered to be the film debut for the "First Lady of the Theatre". Shown in flashback, the pre-Code film told the story of Claudet, who had turned to prostitution to support her illegitimate son after being abandoned by her boyfriend and her family.

The other nominees in the category were Marie Dressler ("Emma") and Lynn Fontanne ("The Guardsman").

Answer: Katharine Hepburn

For her third film, Katharine Hepburn received her first Oscar for her role as aspiring actress Eva Lovelace in "Morning Glory". In the film, Lovelace was a stage-struck small town girl who finally got the role she desired thanks to her friendship with a playwright (Douglas Fairbanks, Jr.) and then had to choose between love and success.

Hepburn was relatively new in Hollywood at the time, but she was able to persuade the writer to model the character, which was originally based on Tallulah Bankhead, to fit her own personality. Years later, Hepburn would say of her performance: "I should have stopped then. I haven't grown since".

The other nominees for Best Actress were May Robson ("Lady for a Day") and Diana Wynyard ("Cavalcade").

Answer: Claudette Colbert

Claudette Colbert won the Academy Award for Best Actress for her role as spoiled heiress Ellie Andrews in "It Happened One Night", the first film to win the "Big Five" Academy Awards: Best Picture, Best Director (Frank Capra), Best Actor (Clark Gable), Best Actress (Colbert), and Best Writing (Robert Riskin).

In the film, a reporter (Gable) agreed to help Andrews reunite with her fortune-hunting husband against the wishes of her family in exchange for an exclusive story, but he ended up falling for her along the way.

The other Best Actress contenders were Grace Moore ("One Night of Love"), Norma Shearer ("The Barretts of Wimpole Street"), and Bette Davis ("Of Human Bondage"). Davis had been a write-in candidate for the award; apparently there was an uproar when she didn't receive a nomination for her performance, so the Academy decided to allow write-in candidates for the awards.

The option was rescinded after the 8th Academy Awards ceremony. Colbert was convinced that Davis would win the award so she decided to take a trip instead of attending the ceremony.

After she was announced as the winner, she was brought from the train station to accept her award in her traveling suit.

Answer: Bette Davis

At the 8th Academy Award ceremony in 1936, Bette Davis won her first Oscar for her role as has-been actress Joyce Heath in "Dangerous". In the film, Heath was rescued by an architect (Franchot Tone) who had admired her during her heyday and was determined to get her back on the stage despite her warnings that she was a jinx and would destroy him. Davis considered her win to be a consolation prize for not winning the award the year before for her performance in "Of Human Bondage". The other nominees in the category were Elisabeth Bergner ("Escape Me Never"), Claudette Colbert ("Private Worlds"), Katharine Hepburn ("Alice Adams"), Miriam Hopkins ("Becky Sharp"), and Merle Oberon ("The Dark Angel").


At the 11th Academy Award in 1939, Bette Davis picked up her second Oscar for her role as spoiled Southern belle Julie Marsden in "Jezebel". The role was reportedly given to Davis as consolation for losing out on the role of Scarlett O'Hara in "Gone with the Wind". In "Jezebel", banker Pres Dillard (Henry Fonda) broke off his engagement to Marsden due to her behavior, and while she stubbornly waited for him to return, he went north and picked up a Yankee bride. The other nominees for Best Actress were Wendy Hiller ("Pygmalion"), Norma Shearer ("Marie Antoinette"), Margaret Sullavan ("Three Comrades"), and Fay Bainter ("White Banners"). Bainter became the first actress to receive two acting nominations in different categories in the same year; she received a Best Supporting Actress nomination and won the Oscar for her role as Marsden's aunt in "Jezebel".

Answer: Luise Rainer

At the 9th Academy Award ceremony in 1937, Luise Rainer won her first Oscar for her role as Flo Ziegfeld's first wife Anna Held in "The Great Ziegfeld". The fictionalized biopic followed the career of the showman Ziegfeld from his early days as a sideshow promoter to his success on Broadway and to his death in 1932. Held was a Polish/French singer who lived with Ziegfeld as his common-law wife and performed in his Follies in the early 1900s. The other Best Actress nominees were Irene Dunne ("Theodora Goes Wild"), Gladys George ("Valiant is the Word for Carrie"), Carole Lombard ("My Man Godfrey"), and Norma Shearer ("Romeo and Juliet").

The following year, Luise Rainer won her second Oscar for her portrayal of dutiful wife O-Lan in "The Good Earth", making her the first performer to win two Academy Awards and to win awards in consecutive years. Based on the novel by Pearl Buck, the story followed the life of farmer Wang Lung (Paul Muni) and his long-suffering wife O-Lan in pre-WWI China. Reportedly both Buck and producer Irving Thalberg had wanted to use Chinese or Chinese-American actors for the film, but the main characters were portrayed by white actors in Asian makeup for the box office draw. Chinese-American actress Anna May Wang was considered for the role of O-lan but reportedly wasn't allowed to play Muni's wife due to anti-miscegenation rules in the Hays Code. The other contenders for the Best Actress award were Irene Dunne ("The Awful Truth"), Greta Garbo ("Camille"), Janet Gaynor ("A Star is Born"), and Barbara Stanwyck ("Stella Dallas").

Answer: Vivien Leigh

With her first nomination, Vivien Leigh won the Academy Award for Best Actress for her role as assertive Southern belle Scarlett O'Hara in "Gone with the Wind". She was the first British actress to win an Academy Award, and she attended the ceremony with then-husband Laurence Olivier, who was nominated in the Best Actor category for his role in "Wuthering Heights". Based on the Margaret Mitchell novel, "Gone with the Wind" was an epic film set against the American Civil War. Over 1400 actresses were reportedly considered for the role of Scarlett O'Hara before producer David O. Selznick selected Leigh.

He dismissed any criticism over the English actress portraying a Southern belle by pointing out that "Scarlett O'Hara's parents were French and Irish. Identically, Miss Leigh's parents are French and Irish." The other nominees in the category were Bette Davis ("Dark Victory"), Irene Dunne ("Love Affair"), Greta Garbo ("Ninotchka"), and Greer Garson ("Goodbye, Mr. Chips").