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During her free time in high school, Trina began writing rhymes until she caught the eye of Miami rapper Trick Daddy who offered the rapper a guest spot on his single “Nann Nigga” in 1998. The song became Trick Daddy’s lead single from his sophomore album “www.thug.com”, which reached No. 62 on the Billboard Hot 100, and exposed Trina to huge audience. Due to the success Trina signed with Slip-n-Slide Records who issued her debut album “Da Baddest Bitch” in March 2001. Although the rapper failed to maintain creative control the album debuted at No. 33 on the Billboard 200, and stayed there for 29 weeks.
Working alongside Missy Elliot for her sophomore album, Trina had complete creative control over the release, which was released in August 2002. “Diamond Princess” debuted at No. 14 on the Billboard 200 and spawned the singles “Told Y’all” featuring Rick Ross, “No Panties”, and “B R Right” featuring Ludacris. The same year Trina launched her own label Diva Enterprises, which later became DP Entertainment, and signed the nine-year-old rapper Lil Brianna.
Trina’s third full-length album “Glamorest Life” was issued in October 2005 and out-performed both its predecessors, debuting at No. 11 on the Billboard 200. The album was led by the single “Don’t Trip” featuring Lil Wayne, and aided by the single “Here We Go” featuring Kelly Roland. After signing with EMI in 2007, Trina released two mixtapes “Rockstarr Royalty” and “Baddest Chick 2: Reloaded” ahead of her fourth full-length “Still da Baddest” in 2008. Reaching No. 6 on the Billboard 200, and No. 1 on the Top R&B/Hip-Hop chart, the album sold 47,000 in its first week.
Led by the single “That’s My Attitude”, Trina’s fifth studio album “Amazin’” was released in May 2010, and later spawned the hits “Million Dollar Girl”, “White Girl”, and “Always”. In 2011 Trina released the mixtape “Diamonds Are Forever”, which featured the singles “Ghetto”, “Waist So Skinny”, and “Can I”. The single “Beam” arrived in July 2012 featuring GunPlay, as well as the single “Bad Bitch” featuring Lolo Monroe and Shawnna.