He made his debut as Grand Puba Maxwell with the group Masters of Ceremony. Its album Dynamite (1988) was hailed by critics, but because of lack of sales the group soon disbanded and Puba became the lead emcee of Brand Nubian. After their debut album One for All (1990) — covering areas from reggae-influenced hip hop music to new jack swing — Puba left the group after disputes and began a solo career. Around 1997 he rejoined the group, recording a few tracks for various soundtracks leading up to the full-length album Foundation in 1998. In 1999, Grand Puba and Sadat X performed on the track "Once Again" on Handsome Boy Modeling School's concept album So... How's Your Girl? Following Brand Nubian's 2004 record Fire in the Hole, Grand Puba appeared on tracks with Beanie Sigel ("Bread and Butter," also featuring groupmate Sadat X), Missy Elliott ("My Struggles," featuring his onetime collaborator Mary J. Blige), and Ugly Duckling ("Something's Going Down Tonight").
In 2009, Grand Puba released his fourth solo album, Retroactive, featuring production from Q-Tip, Large Professor, Kid Capri as well as fellow Brand Nubians. Puba also appeared on the heavy posse cut "Fresh" together with Cormega, KRS-One, Big Daddy Kane, DJ Red Alert and Parrish Smith of EPMD.
On the song "Old School" by Tupac Shakur Grand Puba was sampled and used in the hook. The sample originates from Grand Puba's verse on the song "Dedication" by Brand Nubian.