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.

8. Do You Want More?!!!??! (1995): This was the record that brought the Roots to the world -- or at least as much of the world as was willing to pay attention. At the time, it was the crew's focus on musicianship and live-band dynamics that brought it the most notice; among those fans looking to see hip-hop expand its horizons, as well as those enamored by the band's heavy jazz influence, Do You Want More?!!!??! was a revelation. Really, it was the sound of an act grounded in live jams and experimentation figuring out its way around a proper studio and more cohesive song structures. For this reason, as great as it sounded back then, it falls short of what the Roots would accomplish once they got a better sense of themselves as composers. Viewed by many as their official debut, this established the original sound of the band -- as well as the musical visions and influences of Trotter and Thompson -- but it did so more by capturing their live vibe than creating a classic release. As with The Tipping Point, the tracks that stand out ("Proceed," "Mellow My Man," "Datskat," "Essaywhuman?!!!??!") really stand out, but much of the remainder tends to blend together.

7. How I Got Over (2010): Following a pair of extremely dark, political albums, the Roots paid tribute to the crossover between their hip-hop and indie-rock fanbases by embracing a series of collaborations with acts including Joanna Newsom, Dirty Projectors, and Monsters of Folk. While it sounded great in theory, the finished result falls short of its potential. Or perhaps it just fell victim to it. Where the preceding two albums were noticeably energized and inspired, How I Got Over feels subdued -- perhaps a bit too subdued. While the album is a very cohesive listen, it's also overly sobering at times, often leaving you thinking about which Roots album to throw on next as a more action-inducing antidote. The two strongest tracks, "Walk Alone" and "Dear God 2.0" come close to the top, so from there on out, it's difficult for things not to start going downhill. Overall, the chances the band took here are admirable, the guest list is impressive, and the results often deliver, but it's still too much of a mishmash to rank with the crew's finest work.

6. Rising Down (2008): Rising Down is an album with something to say. Or a few things to say, really, none of them very sunny. It's clear from the album's cover, a cartoon depiction of antiquated racial stereotypes. It's clear from the sequencing, as the record both opens and closes with recorded conversations in which the band members basically lose their shit in reaction to the treatment they're receiving from their label. This is a political, anti-industry, current-events-oriented, angry collection of songs -- and fortunately the Roots are often at their best when they're looking to make a point. If it falls short, it's only because its immediate predecessor, 2006's Game Theory, operated in much the same mindset, and did it more cohesively. Still, with rallying tracks like "I Will Not Apologize," "I Can't Help It," and the title track (featuring longtime collaborator Mos Def), Rising Down makes its point in an impressive way. Plus, in scrapping the inclusion of "Birthday Girl," the band's strangely out-of-character pop song with former Fall Out Boy frontman Patrick Stump, they did the album the biggest favor they could have, by not allowing it to undermine itself.

5. Illadelph Halflife (1996): A clear progression from Do You Want More?!!!??!, the Roots' second major-label album still indulged heavily in jazz-based jams and the power of the extended groove. However, by this point, the band had mastered the form, both perfecting its now-trademarked brand of musical synthesis and taking it as far as it could before getting ready to move on. Indeed, what the Roots would do next would be a defining moment in their career, which places Illadelph Halflife at the apex of the collective's first chapter. The record featured the band's biggest mainstream success to date with "What They Do," a song (and accompanying video) that skewers the more ridiculous trappings of the hip-hop lifestyle. It's both a statement and a manifesto -- with it, the Roots both embraced being an alternative to popular music and painted a picture for where they could (and would) help it go.

4. Game Theory (2006): For most acts, a record like Game Theory would be almost impossible to top. As a statement on modern life, it's impeccable; as an album, it's near perfect. The spirit of J. Dilla looms large here -- the producer's tragic passing occurred during the creation of the record, and his unmistakeable production is featured on album closer "Can't Stop This." Spoken tributes to the artist also feature both in the intro and outro, while in between the Roots basically step up to rage against the world. The picture they paint through insightful, frustration-laced tracks like "False Media" and "Don't Feel Right" is frequently a bleak one, but it's simultaneously eye-opening. By engaging their most impactful songwriting skills, the Roots create a world where the medium and the message have equal weight. The highlights also include "In The Music," a modern anthem featuring the return of old-school member Malik B, whose own personal struggles were the subject of a track on the band's previous album. And then there's "Here I Come," a bold rallying cry that's as welcome as it is unforgettable.

3. Undun (2011): With their most recent album, the Roots flipped the script yet again, producing the first concept record of their career. For the band that had recently been more known for its late-night TV gig with Jimmy Fallon, it was unexpected to say the least. Not only does the album tell the tragic tale of the fictional Redford Stephens, a victim of drugs and gang life who never makes it out of his 20s, but it does so in reverse, taking us from his violent end back to before things all went wrong. It's not the concept that makes this album so powerful -- it's the music itself; some of the finest, most intricate, and hardest-hitting of the group's career -- but that is what ties it all together. Perhaps the Roots have reached a point where they need to look to new sources and think in new ways to find fresh inspiration, but the fact that they're doing just that is exactly why they remain as exciting today as they were 20 years ago. The accompanying videos and multimedia app that further flesh out the world of Undun just show how much care they're giving to what they create, and emphasize that, despite their often lighthearted demeanor on the small screen, this remains an extremely serious band.

2. Phrenology (2002): Coming on the heels of the album that would set the high benchmark for the Roots' entire career, Phrenology had its work more than cut out for it. What the band did in its creation, however, was nothing short of an act of brilliance. Rather than trying to outdo themselves, Black Thought, Questlove, and company instead took a left turn and stretched their musical arms as wide as they could go. Incorporating punk rock, funk, soul, and R&B, the crew undertook what remains its most ambitious project to date, one that was both shocking and revelatory at the same time. Its 10-minute opus "Water," chronicling missing band member Malik B's battle with his personal demons, is among the band's finest output, while "The Seed (2.0)," featuring Cody Chessnutt, remains one of its most recognized and loved compositions. From the Bad Brains-inspired thrash of "!!!!!!!" to the irresistible jam of "Break You Off," this is an album that has something new to reveal on every listen, and is best appreciated in its fantastic, multifaceted entirety.

1. Things Fall Apart (1999): While a case can be made for shuffling around many of the entries on this list, it's hard to imagine anyone tackling this feature and not confidently placing Things Fall Apart at the top. A watershed moment not just for the Roots, but for hip-hop in general, this album saw the band emerge from the jazz-laced cocoon of its original incarnation and take its place as a unique musical force. The songwriting is impeccable, the performances are untouchable, and the album as a whole is seamless. Featuring guest spots from likeminded artists including Common, Mos Def, and Erykah Badu, Things Fall Apart marks the moment the Roots stopped showing potential and started a movement of their own. From its poignant, Chinua Achebe-inspired title to the social commentary of its multiple album covers and Spike Lee sample, this was where the Roots began making the best music of their lives, while also clearly having something to say. The single "You Got Me," featuring Badu on a vocal hook written by Jill Scott, still endures as a classic, set among a series of other classics including "The Next Movement," "Double Trouble," "Act Too," and "Dynamite!" It's an album that sounds less like the work of a mere band, and more like the output of a league of hip-hop superheroes, here to save the world through music, or die trying.