Madonna

During a June 9, 1987 episode of The Tonight Show with Johnny Carson, the assumption was that a routine interview with Madonna, the emerging pop sensation, was in store. However, Madonna had a different agenda. With shameless charm, she playfully flirted with Carson, leaving no doubt that the late-night host was quite taken with the Bay City, Michigan native.

Just weeks after this memorable appearance, Madonna embarked on a global tour to promote her “Who’s That Girl” album. Meanwhile, later that same year, the “Like a Virgin” singer pursued an annulment of her marriage to actor Sean Penn, not related to her playful interaction with Johnny Carson, but attributed to irreconcilable differences.