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All four original members of Dru Hill were natives of Baltimore. Mark Andrews and James Green met each other in middle school, and both later became acquaintances of Tamir Ruffin when all three began pursuing careers in the music industry. Ruffin, nicknamed "Nokio" (an alternate spelling of Nokia, the phone corporation) enlisted Andrews and Green (whose respective nicknames of "Sisqo" and "Woody" came from their early years) to form a singing group. The trio added Larry "Jazz" Anthony, an opera student, to complete their lineup. The group was named "Dru Hill" after Druid Hill Park, a section of Baltimore.

The quartet made a name for itself by getting jobs at a local fudge factory, where they sang to entertain guests while making the candy. Most of their early repitoire was made up of gospel music, as Woody came from a strict Christian family. After the group switched to R&B, Woody's mother pulled him out of the act until the other three convinced her to allow him to remain.

Dru Hill's big break came in 1996, when manager Haqq Islam arranged for them to perform at the Impact Convention in May. The group was signed to Island Records shortly afterward through a production deal with Islam's University music and immediately began recording their debut album. The self-titled Dru Hill was released on November 19 1996, and went on to sell over 500,000 copies, attaining gold status. The group's first single, "Tell Me", was featured on the soundtrack to the Whoopi Goldberg film Eddie, and was a Top 5 R&B hit in the United States.

Stylistically, Dru Hill was the middle-ground between the smooth and gentlemen-like Boyz II Men and the self-proclaimed "bad boys of R&B", Jodeci. Dru Hill received a lot of criticism from a number of people, including the members of Jodeci, for what was perceived was a direct rip-off of Jodeci's vocal and visual stylings, particularly frontman Sisqo's K-Ci Hailey-esque lead vocals. Other major influences for the group included Stevie Wonder and 1980s boy band New Edition.

While Dru Hill's early work relied upon the talents of songwriters/producers such as Daryl Simmons and Keith Sweat, the members, particularly Nokio and Woody, did some of the writing on their first album, including the single "Five Steps". Nokio also did some co-production, and would become the group's main producer by 1998.

Although all four members took turns singing lead, Sisqo made the biggest impression on audiences with his dynamic dancing style, David Ruffin-style emoting, and bleached-blond hair. The Sisqo-led "In My Bed" was the band's first Top 5 pop hit and first #1 R&B hit, and Jazz took the lead on the third single "Never Make a Promise", another #1 R&B hit. The 1997 "Never Make a Promise" music video starred Michelle Thomas as Jazz's girlfriend, and was noted for its message against child molestation.