The ten most enigmatic figures in hip-hop

Categories: Lists

4. Jay Electronica
Jay Electronica is probably the most talented rapper to never put out a studio album. Signed to Jay-Z's Roc Nation label, Jay Elec has equal chance to be the next Hova or the next Lauryn Hill -- that is, one of the greatest ever or massive underachiever. The poeticism of his lyrics are virtually unmatched and his debut mixtape Act 1: The Eternal Sunshine (The Pledge) was actually one of the best concept "albums" of 2007, but since catching fire in 2009 with "Exhibit C," he has fallen off the map almost completely, at least for music. He's made headlines for his affair with Kate Rothschild, heiress to one of the world's largest fortunes, a strange match for him considering his vagabond-ish spirituality.

3. Kool Keith
If eccentricities were dollars, Kool Keith would be the richest rapper in the world. As it stands, Keith remains on the fringes of the popular hip-hop scene, having merely influenced many of your favorite rappers and nearly half of this list: DOOM, Deltron 3030, Captian Murphy and RiFF RaFF, to name a few. When Dr. Octagonecologyst came out in 1997, it was an instant underground classic, if not for its irreverent humor, then for its absolute originality. Like DOOM, Keith has several distinct characters that exist in the same universe and sometimes interact. But all of Keith's characters share a love for the same surrealism, anti-rhyme and non-sequitor that make him one-of-a-kind and possibly off his rocker.

Most rappers have an alternate persona, but nobody takes the role of their characters as seriously as Daniel Dumile, and though DOOM's true identity has long since been revealed, his lyrics and behavior continue to baffle critics and fans alike. DOOM performs behind a mask, taking the effect of his appearance on his music into his own hands. His explanation from "Beef Rap": "He wears a mask just to cover the raw flesh/A rather ugly brother with flows that's gorgeous." But perhaps most perplexing has been his practice of hiring an impersonator to perform behind the mask at his shows instead of him. His explanation is that he is a performance artist, not simply a rapper, and he's fulfilling his super-villain role, but there's no doubt that he's estranged many a fan with his unconventional (non)performing habits.

1. Lil B
Lil B makes no attempt to disguise any part of himself, nor does he veil his lyrics and intentions in abstractions. Still, the creator of the #BASED movement which nobody seems to be able to define is the most argued about rapper on this list and possibly ever. One moment, he'll be a libido-driven maniac, and the next moment, he'll be an eternal spring of positivity. Some fans claim that he is a troll, a caricature of the modern ultraviolent and sexist rap that almost manages to caricature itself. Others claim he is almost Ghandi-like in his beneficence. Detractors say he plain straight can't rap. All of these assessments are true to some degree; Lil B is a complex human (aren't we all?), exposing his every side in a manner similar to abstract expressionism. Who knew that unadulterated humanity could be so hard to pin down? But regardless of what you believe, every Lil B fan agrees on some things: He's the BasedGod, his inexplicable whooping is infectious, he fucked your bitch and he is the greatest rapper of all time.

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