Hide the kiddies, at least temporarily: 11 famous children’s entertainers with adult sidelines

1. Shel Silverstein
Our culture holds few things more sacred than the purity and innocence of children. Children’s entertainers are consequently held to a much higher standard than performers who cater to adults. Much of the shock that greeted Paul Reubens’ 1991 arrest for indecent exposure stemmed from the tragicomic gulf between the eminently presentable, clean-cut Pee-wee Herman beloved by children everywhere and the weird, creepy, all-too-fallible human being in the mug shot. But children’s entertainers are just as human as everyone else, and some have embraced decidedly adult sidelines that contrast dramatically with their kiddie-approved oeuvre. Take Shel Silverstein, for example. Silverstein’s whimsical books of poetry have proved a potent gateway to the art form for generations of children, but the same hands that drew the illustrations for timeless classics like The Giving Tree and Where The Sidewalk Ends also penned naughty Playboy cartoons, essays, and illustrated travelogues for decades. The penchant for rhyming verse that made Silverstein a kiddie icon also inspired irreverent country songs, for himself and others, that reflected the tenor of the times. And by “reflected the tenor of the times” we mean “are chockablock with pot references.” With song titles like “The Smoke-Off” and “I Got Stoned And I Missed It,” he wasn’t exactly subtle with his drug innuendo, but Silverstein’s primary contribution to country naughtiness was indirect: According to pop-culture legend, it was Silverstein, hero of children everywhere, who convinced buddy David Allen Coe that he should release his X-rated, “ironically” racist, and sexist outlaw songs on the underground market. And the world was much richer for it.
2. Roald Dahl
The great thing about writers like Roald Dahl is that they’re on the shelf patiently waiting for readers at every stage of development. Kids can start around first grade with Dahl’s youngest works, like The Twits and Esio Trot, or the kids’ poetry books Revolting Rhymes and Dirty Beasts. Then they can eventually graduate up to slightly older fare, like Charlie And The Chocolate Factory, Matilda, and The Witches. For young teenagers, there are his accessible but slightly horrifying biographies, Going Solo and Boy; older teenagers will have a lot of fun with his extensive collection of sharp, smart, twist-ending short stories, collected in omnibuses like Tales Of The Unexpected. And whenever readers are ready, they can graduate up to his frank, ribald sexual comedies, like the novel-in-stories My Uncle Oswald or the collection Switch Bitch. The title story in the latter is about a carefully planned secret wife-swap, with two neighbors learning each other’s sexual routines, then slipping into each other’s beds for a night. That’s par for the course in Dahl’s adult fiction, which is playfully lurid, fairly sexually explicit, and just as cruelly funny as his material for kids.
3. J.K. Rowling
In the lead-up to the release of The Casual Vacancy, the first adult novel from Harry Potter mastermind J.K. Rowling, many pearls were clutched over the so-called “dirty bits” that spilled from the same pen responsible for the world’s most beloved boy wizard. News outlets snickered and clucked over the reported presence of words like “nipple” and “shag”—not to mention the frank acknowledgement and semi-graphic depiction of sex—apparently unable, or unwilling, to process these elements outside of the all-ages context of Harry Potter. (Gawker went so far as to catalog every instance of said dirtiness, subbing in Harry Potter characters in the quotations from the book.) The reality of The Casual Vacancy is not half as bad as the gleefully scandalized reactions would indicate; the profanity is only exceptional when compared to Harry Potter—which The Casual Vacancy has precisely nothing in common with—and while the sexual bits are frank and awkward (and somewhat overwritten), they’re about as titillating as the novel’s prosaic plot, about the petty battle over a small-town local election. But since it’s all but impossible to separate Rowling from her most famous creation, the moderate indecency of The Casual Vacancy is magnified—and ick-ified—through the distorting lens of Harry Potter.
4. Daniel Handler
Creativity can’t always be divided into neat little categories. So it shouldn’t be surprising that the qualities that distinguish the fare of beloved children’s entertainers can also be found in their more adult-oriented projects. That’s certainly true of a prodigiously talented renaissance man born Daniel Handler but better known to children everywhere as his pen name and alter ego, Lemony Snicket. The gothic dark humor and devastating wit that characterizes the bestsellers Handler writes as Snicket can also be found in outside projects like Watch Your Mouth, an adult novel he published under his own name, and Rick, a 2003 dark comedy of moral corruption starring Bill Pullman, who has always made for a better heel than hero and delivers one of his most memorable yet overlooked turns as a corporate schemer with a bank ledger for a soul and a black hole where his conscience should be. The strangely simpatico Watch Your Mouth and Rick are both heavily inspired by Handler’s love of opera—Rick is loosely based on Rigoletto—and feature heavy intimations of incest that mark them as unmistakably adult fare, albeit adult fare filled with the malevolent wit of Handler’s Lemony Snicket novels.
5. Jim Henson
Jim Henson was already a legend of the children’s entertainment field thanks to Sesame Street when a hip Canadian television producer named Lorne Michaels sought him out for a new, decidedly adult live sketch program he was creating. In its first season at least, Saturday Night Live had a distinct variety-show vibe: The show featured everything from stand-up to short films to musical performances and even magic and the occasional dance troupe. So there was a certain logic to including fantastical, albeit physically repulsive, puppets voiced and operated by Henson and his associates, in sketches set in the depressing fictional fantasy land “The Land Of Gorch.” Alas, Jim Henson’s puppets and the original incarnation of Saturday Night Live ended up being two great tastes that tasted dreadful together. Head writer Michael O’Donoghue famously refused to write for the Henson segments with his quip, “I don’t write for felt,” and the segment’s dark humor and intentional grotesqueness was more off-putting and weird than transgressive or fun. The live audience for Saturday Night Live tolerated the segments at best; not surprisingly, Henson and SNL soon parted ways, and Henson went back to entertaining sweet, innocent, pure-hearted children instead of the belligerent stoners that were Saturday Night Live’s original and most important audience.