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9. The Tipping Point (2004): Following immediately the two most groundbreaking, progressive records by any band more than a decade past their debut, The Tipping Point felt like a step backward -- an eschewing of the complex songcraft and musical exploration the Roots had been pushing through the dawn of the new century. It's not a bad album by any stretch, but its place in the band's chronology is confusing. Bypassing hooks for the most part, The Tipping Point is more of a meandering effort, focusing on grooves and jams rather than giving the listener anything solid to hold on to. Of course, that's a big part of what made the Roots so popular in the first place, so perhaps it was more of a reaction to where they had been than where they were going. There are a few standout tracks that leave their mark and beg for the replay button -- most notably the ingeniously mumbled "Don't Say Nuthin" and the yearning album closer "Why (What's Going On?)" -- but as a whole, The Tipping Point tends to lean toward the less memorable end of the scale.