The group began as Pardlo signing on as a solo artist. However, soon Pardlo's high school friend Toby, and the producers decided that it should be a two-man group featured in the album. Soon after the two-man group began to work on the album, The Product G&B became successful. In order to stand out, the producers decided to add a female member. They chose Ortiz, a schoolmate from Pardlo and Toby's high school. During production, all three members did writing on the songs. The trio focused on trying to make lyrics that told a story, Toby noting that he got some inspiration for writing songs that tell stories from country music. A large amount of the songs are based on real-life experiences the trio has experienced, such as "What Would You Do?".
"What Would You Do?" was featured on the soundtrack to the 1999 film Life. However, it was not formally released until 2001.
This helped with the sale of the album once it was released, and the album became a hit. The group disbanded in 2003, failing to release another album, despite their debut's success.
The album received generally favorable reviews. Allmusic's Jon Azpiri noted "it stands as an impressive debut". Jon Caramanica of Rolling Stone said that, although "today's bling-tastic R&B usually avoids social commentary", City High's debut "hinges on thick, stomp-worthy funk, luxurious soul grooves and plaintive harmonies about messy modern love".RTE Entertainment's John Raftery raved that "'City High' seem to be part of a movement, alongside Lucy Pearl and Spooks, which is letting the world know that black America is about more than just blunts and guns. That alone makes this classy album stand out from the crowd."Q magazine said that "few have managed to capture the original Fugee spirit like City High". In a mixed review, Maurice Bottomley of Pop Matters felt that some songs have poor lyrical content, including "City High Anthem"'s "collection of clichés beyond any chance of redemption", and said that "15 Will Get You 20" is "catchy to the point of irritation".
"Caramel" was the second single by the group. Although not as successful as their first, it still managed to peak at nine on the Hot R&B/Hip-Hop Singles & Tracks and eighteen on the Billboard Hot 100.
"City High Anthem" was intended to be the third single by the group, however it was unsuccessful and did not chart.