* David Bowie: While not the first, Bowie's flamboyant style in the 70s, including his signature lightning bolt earring, played a significant role in making double earrings more acceptable for men.
* Johnny Depp: His iconic role as Captain Jack Sparrow in "Pirates of the Caribbean" in the early 2000s cemented the image of a male pirate sporting multiple earrings.
* Other notable figures: Many other musicians, actors, and artists in the 70s, 80s, and 90s, such as members of rock bands like The Cure, The Smiths, and Duran Duran, contributed to the trend.
It's important to note that men have worn earrings throughout history in various cultures. The "first" is difficult to determine with certainty, but the individuals mentioned above helped bring it to mainstream acceptance in the modern era.