Little Brother formed at North Carolina Central University, located in Durham. Phonte (born Phonte Lyshod Coleman), Big Pooh (born Thomas Jones), and 9th Wonder (born Patrick Denard Douthit) had known each other since 1998, when they performed in a local hip-hop outfit called the Organization. After that group's dissolution in 2000, they anchored a 12-member crew dubbed the Justus League. The trio worked together off and on in varying combinations until they officially teamed up as Little Brother in August 2001, adopting the name as a humble nod to their influences. Their first recording together was "Speed," a playful, down-to-earth look at the pressures of holding a day job while trying to make it in the music business. It set the tone for much of their early material. Over the next few months, they developed enough of a repertoire to start performing live around the area and quickly earned a following.
When the group made their music available for download on the Internet, a substantial buzz built far outside North Carolina, and it eventually earned them a deal with the Oakland-based ABB Records in 2002. In 2003, Little Brother released their full-length debut, The Listening, which won widespread critical praise that focused especially on 9th Wonder's production. The buzz helped him earn a raft of high-profile outside gigs, including tracks on a pair of multi-platinum releases: The Black Album by Jay-Z and Destiny Fulfilled by Destiny's Child. Little Brother leapt to major-label Atlantic for the The Minstrel Show, a highly satirical and uncommercial set that entered Billboard's R&B/hip-hop chart at number 19 in 2005. In 2007, as the group was finishing up their third album, it was announced that they had left Atlantic and had become a duo with the departure of 9th Wonder. After its release later that year, Getback — which featured one 9th Wonder-produced track with Illmind, Nottz, Khrysis, and Zo! also among the contributors — nonetheless debuted at number 18 on the R&B/hip-hop chart.
Amid significant activity outside the group — Pooh's solo discography was lengthening, while Phonte was busy with the Grammy-nominated Foreign Exchange — Little Brother made it known that a hiatus would follow their next album. That set, Leftback, arrived in 2010, after which Phonte and Pooh continued down separate, occasionally intersecting paths for nearly a decade. The MCs and 9th Wonder reconvened in 2018 to perform at Durham's Art of Cool Festival (as a last-minute replacement for Royce da 5'9", who missed his flight). Phonte and Pooh then took it to the studio for a fifth proper Little Brother album, May the Lord Watch, which arrived within a year of the MCs' reconnection. Among the producers were past associates such as Khrysis, Nottz, and Zo!, along with the likes of Focus..., Black Milk, and Devin Morrison. ~ Steve Huey & Andy Kellman