"U Should've Known Better" is a song by American recording artist Monica. It was written in collaboration with Harold Lilly and Jermaine Dupri, and produced by the latter along with frequent co-producer Bryan Michael Cox for her original third studio album, All Eyez on Me (2002). When the album was shelved for release outside Japan, the song was one out of five original records that were transferred into its new version, After the Storm (2003). A contemporary R&B slow jam, "U Should've Known Better" contains elements of soul music and rock music. Built on an pulsating backbeat, the song's instrumentation consists of screeching guitars and an understated harp pattern. Lyrically, Monica, as the protagonist, delivers a message of loyalty to her imprisoned love interest and sings about staying down for him despite his doubts.

The song was generally well received by contemporary music critics who highlighted the heartfelt emotion and sadness. Released as the fourth and final single from After the Storm in May 2004, the single marked Monica's first balladic release in over five years. On the charts, "U Should've Known Better" peaked at number 19 on the US Billboard Hot 100 and number 6 on the Hot R&B/Hip-Hop Singles & Tracks, becoming the album's highest-charting single release after "So Gone". Its accompanying music video was shot by director Benny Boom, and filmed in Mexico in April 2004. It features rapper Young Buck as Monica's love interest.

...
Wikipedia