1. Naughty By Nature, "Mourn You Til I Join You" (available on Greatest Hits: Naughty's Nicest)
"Damn, I wish they knew how much you loved New York," goes the most heart-wrenching and revelatory line in "Mourn You Til I Join You," Naughty By Nature's posthumous tribute to Tupac Shakur, a buddy of frontman Treach. Before 2Pac was a West Coast O.G., he was a New York theater geek, and "Mourn You Til I Join You" memorializes his life before it reached iconic status, irreverently but affectionately documenting his carefree existence back when he was just a hyperactive roadie for Digital Underground, desperate to make a name for himself in movies and music.
2. Talib Kweli, "Ms. Hill" (available on Right About Now)
On "Ms. Hill," Talib Kweli wrestles with the complex, contradictory legacy of Lauryn Hill, sensitively exploring the way her unwillingness to compromise with a corrupt music industry has transformed her into a veritable recluse. As Kweli himself acknowledges, "Ms. Hill" is a platonic love song, the work of a man infatuated both with what Hill has accomplished and with what she might still achieve.
3. Nas, "U.B.R. (Unauthorized Biography Of Rakim)" (available on Street's Disciple)
Over a beat as chilly and remorseless as the grave, Nas pays reverent homage to one of his creative idols on the awkwardly titled "U.B.R. (Unauthorized Biography Of Rakim)." For some reason, Nas begins by thanking God and his children before launching into a vivid Cliffs Notes take on rap's golden age and Rakim's revered place within it. Things get fuzzier the closer the narrative gets to the present, complete with a clunky "epilogue" in which Nas glumly notes that Rakim's comeback album with Dr. Dre was "dismantled because of creative differences." He sounds more like a publicist than a rap historian.
4. The Roots, "Water" (available on Phrenology)
Phrenology's most sonically abstract song, the three-movement, 10-minute "Water" is also its most emotionally direct effort, lyrically. In the disc's emotional centerpiece, Black Thought poignantly retraces his long, auspicious history with partner in rhyme Malik B, who was reportedly kicked out of The Roots after a long, losing struggle with drug addiction and personal demons. With a potent combination of empathy and tough love, Black Thought urgently admonishes his former bandmate to halt his march toward self-destruction. "Water" is that rarest of anomalies: an anti-drug song full of nuance, compassion and craft.
5. People Under The Stairs, "Yo" (available on Or Stay Tuned)
Who says rappers can't be 200-proof mensches? On the lushly produced "Yo," affable People Under The Stairs rappers Double K and Thes One offer gushing testimonials to each other while providing a creation myth for their fruitful ongoing collaboration. Double K lionizes Thes One as a legendary crate-digger who "shines so bright you sneeze when you see him," then recounts the day K told his future partner that he was "feeling all them old jazz loops." Thes One rejects Double K's offer to buy a beat from him, but promises to "dig" him "up a beat like Super Mario 2" gratis. Thes One then describes his "never sober" partner as a "rock star/macktivist." Ain't friendship grand?