City High is an American R&B/hip hop trio consisting of rappers/singers Ryan Toby, Robbie Pardlo and Claudette Ortiz. Originally signed to Wyclef Jean's Booga Basement imprint as a duo, the group became a trio when Jean realized that they resembled another group on his roster, The Product G&B, too much. Ortiz was then added to the group after contributing her vocals to the group's first big hit, What Would You Do from the Life soundtrack in 1999. City High drew comparisons to their mentor's supergroup, The Fugees for two main reasons: the first being that the make-up of the band was two male members and a superstar female member, and also the fact that the members both sang and rapped. Unlike The Fugees, however, City High had more of an R&B slant.

In 2001, "What Would You Do?" was released as part of the band's eponymous debut to radio with a new mix that interpolated Dr. Dre's The Next Episode into the bridge. The song, a story seen from different perspectives about a young woman who becomes a stripper to feed her child, became a U.S. Pop #8 and R&B #13 hit. The band's follow-up single, Caramel, found Ortiz singing lead and Pardlo on the bridge. In the original version, there is also a section where Ortiz sings in Spanish. For radio release, the song was remixed to include the rapper Eve. "Caramel" was a U.S. Pop #18 and R&B #9 hit. The remix was done by Trackmasters. The final single from the group's debut was City High Anthem, which failed to make a big impact on urban and top 40 markets. Once again, however, a remix was released, featuring rapper Styles P.

In early 2002, City High shot several mini music video commercials for MTV based on their own songs promoting the 11th season of The Real World set in Chicago.

Their debut self-titled album sold millions and was nominated for a Grammy Award in 2003. City High members Ryan Toby and Claudette Ortiz got married on October 14, 2004.

City High disbanded in 2003.