Born and raised in Baltimore, Sisqó met future Dru Hill bandmate James "Woody" Green while in middle school. The two of them would later be recruited by Tamir "Nokio" Ruffin to form Dru Hill, named after Druid Hill Park in Baltimore. Larry "Jazz" Anthony was also soon added to the lineup.
Releasing two platinum LPs and a number of successful singles, Dru Hill was a major R&B success during the late 1990s, in no small part because of Sisqó's flamboyant stage personality. In between Dru Hill albums, Sisqó wrote the first two hit singles for labelmate Mya, and appeared with her on the first one, "It's All About Me".
