If you ever spotted Ricky Hil  (formerly Rich Hil) at a party, you'd never believe the tatted up, drug-addicted rebel was the son of fashion mogul Tommy Hilfiger. Born and raised in the affluent Connecticut suburbs, Ricky was surrounded by wealth and celebrities -- including rappers -- due to his father's successful clothing company.

Ricky caught the rapping bug as a teen and eventually landed a deal with Warner Bros. Records. As the ever-vigilant gossip news site Gawker has pointed out, Ricky is pretty much the poster child for celeb kids who shouldn't rap.

With over 18 mixtapes -- most notably 'SYLDD' -- and collaborations with artists like the Weekend, Leona Lewis and Kid Cudi, the raspy-voiced Ricky is the rich kid who's made the most strides in establishing a career -- too bad we can't take his grating music seriously.