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Frank Sinatra Trivia

From bobby-soxers to Rat Pack shenanigans, prove you're as cool as Ol’ Blue Eyes in this swingin’ slice of Sinatra trivia!

EXAMPLE QUESTIONS

Born December 12, 1915, to Italian immigrant parents, in which New Jersey city was he born?

Hoboken

Which 1940 Tommy Dorsey recording became his first No. 1—topping Billboard’s inaugural retail chart for 12 weeks—and nudged him toward a solo career?

I'll Never Smile Again

In the 1950s–60s, the Rat Pack turned casino stages—like the Copa Room at the Sands—into legendary hotspots in which U.S. city?

Las Vegas

Which song won him the 1967 Grammy for Record of the Year?

Strangers in the Night

Which 1953 film earned Sinatra an Oscar for Best Supporting Actor, reviving his career?

From Here to Eternity