He was assisted by Tadd Mingo, and Javier Valeverde. William Odum played the guitar, while recording at the SouthSide Studios in Atlanta, Georgia was overseen Brian Frye. "U Should've Known Better" was mixed by Phil Tan with further assistance from Dupri and John Horesco IV. Monica penned the song along with Harold Lilly and longtime contributor Jermaine Dupri, while production on the track was helmed by Dupri and Bryan Michael Cox. The song was co-written and produced by mentor Jermaine Dupri. Though she "had never thought about writing much" by then, her producers encouraged the singer to intensify her work on the All Eyez on Me album and to write and contribute own lyrics and ideas to the songs, one of which was the ballad "U Should've Known Better." Throughout the process, Monica primarily worked with her usual stable of producers, which included Dallas Austin, production team Soulshock & Karlin, Bryan Michael Cox, and Rodney Jerkins and his Darkchild crew. In early 2001, Monica eventually decided to resume recording to prepare the release of her third album in fall 2001. Knot left behind a daughter from a previous relationship, who Monica took into care after going into hiatus. In July 2000, Monica and Weems were together at the graveside of Weems's brother, who had died in an automobile accident at age 25 in 1998, when Weems, without warning, put a gun to his head and shot himself to death. The following month, personal tribulations put a temporary halt on the album's production when her former boyfriend Jarvis "Knot" Weems committed suicide. In an interview with MTV News in June 2000, Monica revealed that she was planning to start work on a follow-up to her 1998 album The Boy Is Mine throughout the summer season, with a first single to be released by October of the same year. It features rapper Young Buck as Monica's love interest. Its accompanying music video was shot by director Benny Boom, and filmed in Mexico in April 2004. 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".
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Released as the fourth and final single from After the Storm on March 8, 2004, the single marked Monica's first balladic release in over five years.
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The song was generally well received by contemporary music critics who highlighted the heartfelt emotion and sadness. 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. Built on an pulsating backbeat, the song's instrumentation consists of screeching guitars and an understated harp pattern.
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A contemporary R&B slow jam, "U Should've Known Better" contains elements of soul music and rock music. 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). 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). " U Should've Known Better" is a song by American recording artist Monica.