On paper, The Showdown: The Sugarhill Gang vs. Grandmaster Flash and the Furious Five seems like a good idea. Take two of the greatest old-school hip-hop groups, pair off six of their best tracks each, offer commentary and insight from Chuck D and Ice-T, and then see who wins. It's a cute, clever idea, but halfway through the album, it becomes tiring -- you no longer find the "boxing match" amusing, you just want to hear the music, especially since the music is so good. Of course, it's possible to program around the sketches, and then you'll just have a really good collection (including a previously unreleased cut from the Sugarhill Gang, "One for the $"), but most listeners will be happier with collections devoted to either artist.
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AllMusic Review by Stephen Thomas Erlewine