Shel Silverstein was kicked out of one college and dropped out of another, and he described those days gloomily: "I didn't get laid much. I didn't learn much. Those are the two worst things that can happen to a guy." His trouble with the ladies didn't persist. Ozy recalls what for many is a less-known side of the famed cartoonist's life: that of, in the words of David Mamet, "Hugh Hefner's sidekick." After scraping by as a freelance cartoonist for a few years, Silverstein got his first real job under the wings of Hefner, traveling the world as Playboy's foreign correspondent cartoonist. And women soon flocked to him, reports Ozy. "Shel was not handsome," one friend said. "Maybe it was his eyes; they would twinkle and pierce simultaneously, giving you the impression that he knew something you didn't."
By the time the first Playboy Mansion was built in 1959, Silverstein was in the inner circle, known to spend weeks and even months partying within its confines. Lisa Rogak, author of the 2011 biography A Boy Named Shel, believes he slept with hundreds—perhaps thousands—of women, per a 2014 New Yorker article. His first child, Shoshanna, was born to a Playboy Bunny, reports the Atlantic; the girl died at age 11 from a brain aneurysm, a loss Silverstein reportedly never got over. He also had a son. The Atlantic points out Silverstein was also a songwriter and penned "A Boy Named Sue," made famous by Johnny Cash. Though Silverstein released nine albums, he also recorded some "eye-popping" songs that weren't formally released, with titles like "I Love My Right Hand" and "Get My Rocks Off"; the latter was covered by none other than Marilyn Manson. Read more on Silverstein's Playboy days here. (Playboy itself is changing in a fundamental way in March.)