Boldy James is tied for being the oldest rapper on this list, but unlike the other 31-year-old, he's not exactly a veteran. Boldy James has been kicking around for years but he's so underrated that he doesn't even have a Wikipedia page. We were impressed with Boldy when we happened to catch him tearing up the beat to "JIMBO," a song his cousin Chuck Inglish produced, back in 2011. He recently released his Alchemist-produced album, My 1st Chemistry Set, which has helped his buzz a bit, but not like we were hoping.
We'll admit, he has an uphill climb as he's a bleak street rapper. His raps are as cold and hard as concrete in an era when rappers would rather be singing a chorus than telling tales of slinging rocks. But Boldy is a throwback rapper, build in the image of '90s stalwarts like Prodigy, though he isn't obsessed with reliving the old days. The Detroit rappers' voice and lyrics are reminiscent of of another Midwest spitter, Freddie Gibbs. But unlike Gibbs, he raps at a much more controlled pace, spacing out his words for maximum impact. He's got style too, check out "Moochie," a song in the vein of Big L's "Ebonics." But he's at his best when he's most direct, using an economy of words to tell the story of a murder on "Surprise Party" he ends his verse flatly stating, "That's my story and I'm sticking to it/Could have paid a nigga to do it/But I'd rather I do the shooting." —Insanul Ahmed