15 Best Old-School Rap Albums

9. Gangsta's Paradise €“ Coolio

I know many people may think I'm committing a sin by including this album on my list because they condemn "gangsta rap", but a closer listen to the album's Grammy-winning lead single (which is also parodied by "Weird Al" Yankovic in "Amish Paradise") reveals that Coolio is not applauding the gangster lifestyle but actually criticising it. In fact it's a neat morality play, as he plays the part of a gangster regretting his ways "on his knees at night/saying prayers in the streetlight." Later, he muses, "They say I got to learn but nobody's here to teach me/If they can't understand it, how can they reach me?" and, one of the best lines from any rap song, "Too much television watchin' got me chasin' dreams." "Gangsta's Paradise" would have been enough, but Coolio doesn't stop there. He also boasts the hot club track "1, 2, 3, 4," the smooth single "Cruisin'" that samples the classic of the same name (with an added "g" at the end), and the best condom commercial you'll ever hear; "Too Hot." Coolio's follow-up, My Soul, was almost as decent as this one. And yes, it was more soulful, not only because of the gospel-tinged samples he selected on some of the tracks but also because of his soul-baring lyrics; "Keep the money and the fame 'cause all I wanna hold/is my artistic flavour and control of my soul." Most poignant is his survey of rap music up until that point: "In two decades, rap went from Planet Rock to crack rock/Now everybody got a glock/And it don't stop, 'til another brother drops." He's almost disappeared now (save for the occasional reality show appearance), but face it; the guy was underrated.
 
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Michael Perone has written for The Baltimore Sun, Baltimore City Paper, The Island Ear (now titled Long Island Press), and The Long Island Voice, a short-lived spinoff of The Village Voice. He currently works as an Editor in Manhattan. And he still thinks Michael Keaton was the best Batman.