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9. Lauryn Hill: "Doo Wop (That Thing)"
What can you do but sigh, shake your head, and sing along to this one-of-a-kind pop hit with a seriously bluesy undercurrent running through it? Lauryn Hill never came close to approaching this level of craftsmanship and coolness again, but I really don't think anyone has: "Doo Wop (That Thing)" juxtaposes the new and old, two separate of eras of music that go together better than most people would care to admit. And Lauryn could sway so well in both.