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He signed with Universal and his debut, "Country Boy" was released in 1999. His first album included a respectable six out of thirteen tracks written by himself, and he also played guitar on a couple of songs, while the album was also to feature guests like K-Ci, Monifah and Chico DeBarge, a remake of Bobby Womack's "I Wish He Didn't Trust Me So Much" and productions by Kay Gee and Darren Lighty. The disc earned praise from critics but it didn't make much impact commercially. Later, he also provided guest vocals on other albums, most notably helping the jazz group Pieces Of A Dream (in "Why Don't You Let Me Love You") and the dance singer Sonique (in "Drama"), but most people had forgotten about him until he reappeared on the scene with "More Than A Woman", a duet with Angie Stone included on 2001's "Mahogany Soul". The song, written and produced by Edward "Eddie F" Farrell and Darren Lighty, was intended to be the lead single for Calvin Richardson's second disc from Universal, but the label refused to support the release with a video, then Calvin broke with Universal and passed the song on to Angie Stone, who wanted to record it with Richardson. However, maybe because of rumors regarding Stone's love interest, on the single release Richardson was replaced by Joe and the J label deal evaporated. The album version was included on the Deliver Us From Eva film soundtrack too. Calvin also appeared on two other soundtracks: Friday After Next with the track "Go To The Club" and Bringing Down The House with "Next To You". He also contributed two tracks to Raphael Saadiq's Instant Vintage (2002) and toured with Maxwell and Angie Stone. In the meantime, Calvin Richardson was finishing his sophomore album. Its pubblication was deferred by nine month until September 2003 to have more impact at radio and to take advantage of an opening spot on Nelly's summer tour. The album was called "2:35 PM". There is a story behind the title: Calvin was working hard to finish up in the studio when his girl gave birth to Souljah, his son ("That's my little soul man", explains Calvin). The completion of the album and the birth of his son were so intertwined that Calvin Richardson settled on "2:35 PM", the time that Souljah came into the world. Though most songs were written by Richardson himself, the album included tracks produced by hitmakers like Raphael Saadiq (who returned the favour), Young RJ, Jake And Trev, The Underdogs (Justin Timberlake, B2K), Mike City (Usher, Brandy), Slum Village (Dwele) and The Untouchables (Donell Jones). It deservedly got good sales peaking at number 65 on Billboard's Top100 and at number 8 on Billboard's R&B Chart. In order to promote his image and to increase his popularity Calvin Richardson toured in 2004 with American Idol winner Ruben Studdard.
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