Its original members were lead singer Mark "Sisqó" Andrews, Tamir "Nokio" Ruffin, Larry "Jazz" Anthony and James "Woody" Green.

While Woody's album, Soul Music, was a moderate success in the gospel music industry, Sisqó's debut album, Unleash the Dragon, and its hit singles, "Thong Song" and "Incomplete", were major pop successes, and established Sisqó as a household name outside of Dru Hill.

Dru Hill and rapper Foxy Brown recorded "Big Bad Mama", a remake of Carl Carlton's 1981 hit "She's a Bad Mama Jama (She's Built, She's Stacked)", which was the main single for the soundtrack to the 1997 Bill Bellamy film Def Jam's How to Be a Player.

The group was also instrumental in writing and producing for new University artist Mýa, whose first two singles "It's All About Me" and "Movin' On", were co-written by Sisqó, who also performs guest vocals on "It's All About Me".

At an October 1997 deposition hearing, Eric Kronfeld, president and chief operating officer of Island's parent company PolyGram, was asked why he had hired such an individual.

The Reverend Jesse Jackson became personally involved, publicly stating that the Dutch-based PolyGram had "a pattern of race and sex exclusion.

The single "This Is What We Do", featuring a guest rap from Method Man, set the tone for the group's second album, Enter the Dru.

However, after a shooting incident at a concert in Paris that almost costed two lives of its entourage, member Woody Rock decided to part ways with the group.

[16][17] Def Jam president Kevin Liles, a fellow Baltimore native, pressured the group for a comeback album and a few solo follow-ups, but it never fully materalized.

In 2000, Sisqó and Nokio formed the label, Dragon Records, and signed a girl group named LovHer.

Then, on June 19, 2001, Sisqó released his sophomore solo album, Return of Dragon, but it performed poorly, causing Dru Hill's comeback for the year to be postponed.

[19] After releasing his solo gospel album, Soul Music, in May, and with a new agreement with Def Jam, Dru Hill decided to invite Woody back into the fold while adding a new member, Rufus "Scola" Waller" to the group as its fifth inductee.

He started pushing the group to record a fourth studio album for the label only to postpone the project to focus on artists of his certainty.

In the midst of Dru Hill's label issues, in 2003, Sisqó became involved in a relationship with his stylist Elizabeth Pham, whom he later married on August 17, 2018.

[22] That same year, on June 12, group founder Nokio fathered a son named Niko, whose mother is radio personality Angie Martinez.

[23][24] In early 2008, the original quartet version of Dru Hill began touring alongside fellow 1990s acts Tony!

[3] It focused on their fourth album, InDRUpendence Day, and depicted the progress of returning as a full group, and their work to create new music.