NEW YORK, NY - DECEMBER 05: Willow Smith sighting on December 5, 2011 in New York City. (Photo by Alo Ceballos/FilmMagic)
Alo Ceballos

The ascents of young’ins Willow Smith and Diggy Simmons are both sudden and seemingly lucrative, but their successes are not unprecedented. Every so often, a handful of child rappers bubble into pop consciousness: LL Cool J, Lil Wayne, Foxy Brown, and more recently Soulja Boy, all got their starts as teenagers, while Kris Kross and Lil Bow Wow were even younger. Though many of the mentioned were ushered into fame by seasoned producers or more veteran rappers, what distinguishes Smith and Simmons from adolescent rappers past and present (such as the New Boys and Lil P-Nut) is that they’re already from hip-hop pedigree.

Yet this, too, is not a first: Master P’s son Lil Romeo, for example, benefited greatly from his father’s expertise behind the sound board as well as from his once-hot imprint, No Limit Records, to which Romeo was signed. At the same time, the then-burgeoning rapper also costarred in a number of movies, in one of them alongside his father. Smith and Simmons, like Romeo, are underwritten, if not by assurances of success, by bountiful resources. They’re breaking into entertainment; for them, rap is merely one facet of the fame they seek.

Ten-year-old Smith got into the biz by costarring alongside her father, actor-rapper Will Smith, in I Am Legend. From there, she made a handful more movies, until the Sept. 8 (intentional?) leak of “Whip My Hair” vindicated her dalliance with music. “Whip”—helmed by upstart producer Jukebox, who’d previously worked with the elder Smith on his ’05 album Lost and Found—became a viral hit, though not necessarily a grassroots one.

With a healthy clothing budget and skate-punk haircut to drive home her Lil Rihanna image, Smith had a record deal in place with Hova’s Roc Nation within a mere 48 hours after the ear candy that is “Whip” hit the blogs. (The contract was rumored to be in place even before that.) The tween and Jay-Z, whom she met in Japan over the summer with her family, jointly called into Ryan Seacrest’s radio show to confirm this new with a bit of pomp and circumstance. Just a month later, Smith went viral again, engaging in a Dougie dance-off with Justin Bieber, and yesterday she made her live TV debut on Ellen DeGeneres’ highly rated talk show. A svengali couldn’t have orchestrated her emergence into ubiquity any better.

Diggy Simmons, the son of Run-DMC’s Joseph Simmons, was first introduced to the public on Run’s House, the MTV docu-series about his family. He earned a cult following for his expensive, impeccable style on that show, which spilled over into his attendance at runway shows and his own fashion-driven blog. (Now 15, he even has his own sneaker line called Chivalrous Culture.) The younger Simmons has stalwartly insisted that neither his father nor his uncle, hip-hop impresario/entrepreneur Russell Simmons, ever pulled favors for him. In 2009, his freestyles over Drake’s “Over” and Nas’ “Made You Look” went viral thanks in part to curiosity over whether Run’s rap-gene pool had seeped into his offspring. Still, Simmons proved he had skills, and the latter track caught the attention of rap’s great tastemaker Kanye West.

From there it was highflying: Simmons’ debut mixtape, First Flight, won him a deal with Atlantic Records in March; another mixtape is on the way. Meanwhile, he’s working on a track with Justin Bieber (who’s association with up-and-comers is beginning to seem like a rite of passage) that’s produced by Boi-1da (Drake, Eminem). Simmons is likewise beginning to amass a cache of impressive collaborators that thus far includes artists like Lupe Fiasco and Pharrell Williams.

The talent is there to varying degrees—Simmons with his freestyling, Smith with her scrappy charisma—yet both kids feel like business models. Perhaps this is not a bad thing: For every child rapper who endures (like Lil Wayne, his organic rise being almost nostalgic at this point), countless more will see their stars fade. Hip hop was built on hustle, which has never been a level playing field. So if you have the means, why not start young?