Clara Bow

As the quintessential flapper, she defined the 1920s. Her hairstyle, her clothes, her flamboyant sex life, and her cupid-bow mouth all represented what it was to be in Hollywood in the Jazz Age. Having escaped an impoverished childhood, this beauty took her looks to the bank, starring in over 50 films in the 1920s and early '30s, most notably It (1927), which earned her the moniker The “It” Girl and the first Academy Award winning film, Wings (1927). Her career faltered as talkies took over (her Brooklyn elocution was apparently not a big draw and she was terrified of the microphone), and she retired from film at 26 and got married to cowboy star Rex Bell (who later became the lieutenant governor of Nevada). Her later years were plagued by mental illness and the scandal wrought upon her by her personal secretary, who leaked out lascivious details of Bow's flapper lifestyle when Bow sued her for embezzlement.