She began rapping in the late 1990s under her stage name, Mae West; her rapping skills would eventually gain notice from fellow producer/rapper, Deric "D-Dot" Angelettie, who introduced her via his 2000 solo debut album, Tell 'Em Why U Madd, on the track "Shysty Broads" alongside former Timbaland protégé, Babe Blue. He later renamed her, Lady May, introduced her to Crazy Cat Productions and she eventually landed a contract deal with Arista Records in 2001.
May released her debut single in 2002, "Round Up", which featured R&B singer and former label-mate Blu Cantrell. Her following planned single was "Dick & Doe"; a music video for the song was shot but in the midst of the pushbacks for May Day (first scheduled for a release in May 2002, then to July 16, 2002, then August 2002), the single and video as well as the album were altogether shelved after the poor reception gained from "Round Up" - the album eventually leaked onto P2P sites. She was also featured on former label-mate Rob Jackson's 2002 single "Boom Boom Boom", which was slated to appear on his debut album, For the People, but was eventually shelved as well. In 2003, she was featured on Willa Ford's "A Toast to Men", also appearing in its video.