In the 1920s, the burgeoning movie industry was starting to come into its own, and virtually no actor was as famous - or infamous - as John Barrymore. Like many other film stars his age, Barrymore's career had started in other forms of entertainment, in his case theater, and by the time movies were becoming popular, Barrymore was one of the world's foremost Shakespearean actors. After standout performances in productions of Richard III and Hamlet, Barrymore transitioned for a time to working on films, including Dr. Jekyll and Mr. Hyde (1920), Sherlock Holmes (1922) and The Sea Beast (1926). His career would not be hampered by the end of the silent film era either, and he would continue to star in movies throughout the 1930s, including in critically acclaimed films like Grand Hotel (1932), Twentieth Century (1934) and Midnight (1939).

For a time, Barrymore was one of the most popular actors of the day, but more than 75 years after his death, he is likely better remembered more for his family lineage and his contributions to pop culture, voluntarily and involuntarily. Barrymore hailed from an acting family, and he would become the patriarch whose descendants continued to be acclaimed actors, most recently his granddaughter Drew Barrymore. But while that might be his most tangential legacy in the 21st century, Barrymore's personal life continues to draw interest, from his many marriages and paramours to the substance abuse that was common knowledge by the end of his life. Barrymore even tried to play to his reputation and get in on the joke, often taking on roles that served as parodies of his own outlandish behavior. In a self-deprecating reference to his love life, he once joked, "I am thinking of taking a fifth wife. Why not? Solomon had a thousand wives and he is a synonym for wisdom."