If you wanted to nab the Best Picture Oscar between the late 1950s and 1967, releasing a glossy musical would be as close as you could get to delivering a surefire winner. "Gigi," "The Sound of Music," "Oliver!" and "West Side Story" all took home Hollywood's most prestigious award during this era. Another musical Best Picture winner from this period was "My Fair Lady," which garnered largely positive reviews even if there were a handful of critiques over the casting of Audrey Hepburn in the lead role despite her inability to carry a tune. However, what makes this win questionable for some is that it managed to defeat "Dr. Strangelove" that same year for the Best Picture Oscar.
Kubrick's satire of Cold War-era politics was a hysterical piece of cinema as humorous as it was insightful. Regardless of personal opinions on the films, it's easy to determine which of these two titles was more relevant in the 1960s and, by proxy, more worthy of a Best Picture win. However, comedies haven't been a go-to genre for recognition in the Best Picture category at the Oscars, with only a handful of exceptions (like the 1955 feature "Marty") appearing across the long history of the ceremony. By contrast, musicals were the toast of the Oscars in the 1960s, making it inevitable, if not agreeable, that "My Fair Lady" would beat out "Strangelove."
