All four original members of Dru Hill were natives of Baltimore, Maryland. 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 acronym for “Nasty on Key in Octave”) enlisted Andrews and Green (whose respective nicknames of “Sisqó” and “Big Woody Rock” came from their childhood) to form a singing group. The trio added Larry “Jazz” Anthony, an opera student, to complete their lineup. The group was named after Druid Hill Park, a popular park on the West side of Baltimore, the name of which is pronounced “Dru Hill” in the local accent.
The quartet made a name for itself by getting jobs at a local fudge factory, “The Fudgery,” at the Inner Harbor, where they sang and performed to entertain guests while making fudge (this tradition is still a part of “The Fudgery”).
Most of their early repertoire was made up of gospel music; the group eventually switched to the more commercially viable genre of R&B.
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‘s “Island Black” division 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 became a gold-selling album. 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, gentlemen-like Boyz II Men and the self-proclaimed “bad boys of R&B”, Jodeci. Dru Hill received a lot of criticism, especially from the members of Jodeci, for what was perceived was a direct appropriation of Jodeci’s style, particularly in frontman Sisqó’s K-Ci Hailey-esque lead vocals. Other major influences for the group included Stevie Wonder and 1980s boy band New Edition.
Both the group themselves and songwriters/producers such as Daryl Simmons and Keith Sweat wrote the songs for the Dru Hill album, with the group themselves writing the single “5 Steps”. Nokio also did some co-production, and would become the group’s main producer by 1998.
All four members took turns singing lead, with Sisqó making the biggest impression on audiences with his dancing style, David Ruffin-styled emoting, and bleached–blond hair. The Sisqó-led “In My Bed” was the group’s first Top 5 pop hit and first #1 R&B hit. Jazz took the lead on the third single, “Never Make a Promise”, which became a second #1 R&B hit. “Never Make a Promise”‘s music video starred Michelle Thomas as Jazz’s girlfriend, and was noted for its message against child molestation.