Trina

In 1998, Trina was studying to get her real estate license,[19] when she caught the attention of Miami rapper Trick Daddy, who asked her to appear on his track "Nann Nigga". The song was released as the lead single from Trick's second studio album, www.thug.com on July 14, 1998, reaching #62 on the US Billboard Hot 100 and #3 on the Rap Songs chart. This kickstarted Trina's rap career, leading to a record deal with Slip-n-Slide Records with distribution from Atlantic Records.

On March 21, 2000, Trina released her debut album Da Baddest Bitch,[20] which debuted at #33 on the US Billboard 200 and #11 on the Top R&B/Hip-Hop Albums chart.[21] It stayed on the Billboard 200 chart for 39 weeks and on the Hip-Hop/R&B album chart for 49 consecutive weeks[22] and was certified Gold by the RIAA by November of that year.[23] The album was preceded by the singles "Da Baddest Bitch" on December 22, 1999, and "Pull Over" on February 13, 2000, which reached #93 on the Hot 100, #46 on the Hot R&B/Hip-Hop Songs chart, and #41 on the Rap Songs chart.[24][25]

Trina began working on her second album in 2001 with Missy Elliot,[26] enjoying more creative control than ever before, saying in interviews that the album was "more what Trina's about, how Trina looks, how Trina feels, the things that Trina consists of."[27] During this time, she started her own record label imprint, Diva Enterprises. In September 2002, she signed 9-year-old recording artist Lil' Brianna, who would appear on her track "Kandi" and later be known as Brianna Perry.

On August 27, 2002, Trina released her second album Diamond Princess,[28] which debut at #14 on the Billboard 200 and #5 on the Top R&B/Hip-Hop Albums chart, selling 67,000 units in its first week.[29] The album was preceded by "Told Y'all", featuring Rick Ross, which reached #64 on the Hot R&B/Hip-Hop Songs chart and appeared on the soundtrack to the action comedy All About the Benjamins, and "No Panties", featuring Tweet, which reached #88 on the Hot R&B/Hip-Hop Songs chart and #45 on the UK Singles Chart. On October 22, 2002, Trina released the album's third and final single, "B R Right", featuring Ludacris, which reached #83 on the Billboard Hot 100, #50 on the Hot R&B/Hip-Hop Songs chart, and #24 on the Rap Songs chart.

On October 4, 2005, Trina released her third studio album, Glamorest Life,[30] which debut at #11 on the Billboard 200,[31] #2 on the Top R&B/Hip-Hop Albums chart, and #2 on the Top Rap Albums chart, selling 77,000 units in its first week.[29] The album was preceded by the single, "Don't Trip", featuring Lil Wayne on April 28, 2005, which reached #74 on the Hot R&B/Hip-Hop Songs chart, and "Here We Go", featuring Kelly Rowland, on September 23, 2005, which became one of Trina's most successful singles, reaching #17 on the Hot 100, #8 on the Hot R&B/Hip-Hop Songs chart, and #3 on the Hot Rap Songs chart and Top 20 in most countries worldwide. The single was certified Gold in the US in June 2006.[23] The album's third and final single, "Da Club", featuring Mannie Fresh, was released on November 22, 2005.

Trina performing in 2008.

On May 18, 2007, it was announced that Trina had left Atlantic Records and signed to EMI in conjunction with her original label, Slip-n-Slide Records.[32]

On April 1, 2008, Trina released her fourth studio album, Still da Baddest, which reached #6 on the Billboard 200, #1 on the Top R&B/Hip-Hop Albums chart, and #1 on the Top Rap Albums chart, becoming her first album to top the charts. Its first-week sales were 47,000.[33] The album was preceded by the singles "Single Again", which reached #25 on the Bubbling Under Hot 100, #59 on the Hot R&B/Hip-Hop Songs chart, and #19 on the Rap Songs chart, and "I Got a Thang for You", featuring Keyshia Cole, which reached #21 on the Bubbling Under Hot 100 and #59 on the Hot R&B/Hip-Hop Songs chart. The third and final single from the album, "Look Back at Me", featuring Killer Mike, hit #1 in Denmark.

On May 4, 2010, Trina released her fifth studio album, Amazin', which debut at #13 on the Billboard 200, #4 on the Top R&B/Hip-Hop Albums chart, #2 on the Top Rap Albums chart, and #1 on the Billboard Independent Albums chart. The album sold over 32,000 copies in its first week.[34][35] The album was preceded by the singles "That's My Attitude" on August 21, 2009, "Million Dollar Girl", featuring Diddy and Keri Hilson, on January 12, 2010, which reached #61 on the Hot R&B/Hip-Hop Songs chart and #20 on the Rap Songs chart, "Always", featuring Monica, on April 20, 2010, which reached #42 on the Hot R&B/Hip-Hop Songs chart, and "White Girl", featuring Flo Rida and Git Fresh, on June 29, 2010.

On March 28, 2011, Trina released the mixtape Diamonds Are Forever.[36] It was preceded by the singles "Ghetto", featuring T-Pain, "Waist So Skinny", featuring Rick Ross, and "Can I", featuring Mýa. The mixtape received 4.8 million streams in two days.[37] During this time, Trina was preparing her sixth studio album.[38] On November 9, 2011, Trina announced on MTV RapFix Live that she was no longer signed to Slip-N-Slide Records,[39] the label she had been with since the beginning of her career.

On December 3, 2012, Trina released the mixtape Back 2 Business, which was preceded by the singles "Beam" featuring Gunplay and Iceberg Slimm, and "Bad Bitch", featuring Lola Monroe and Shawnna.[41][42]

On December 17, 2012, Trina appeared as a co-host on the VH1 late night talk show Tiny Tonight! with Tiny, Tamar Braxton and Claudia Jordan.[43]

On March 9, 2015, Trina revealed that she had signed a new imprint venture with Penalty Entertainment.[44] Days earlier, Trina had released the promotional single "Real One" featuring Rico Love, who she said would be the executive producer of her sixth album. On July 21, 2015, Trina previewed its music video on an episode of Love and Hip Hop Atlanta: Afterparty Live! on July 21, 2015.[45] On October 29, Wolfgang Gartner announced that his song "Turn Up", featuring Trina and Wiley, would be featured on the soundtrack for the video game Need For Speed.[46] On November 13, Trina released her single "Fuck Boy", along with a remix of One Direction's "Perfect", both garnered positive reviews.[47][48][49]

On March 21, 2016, the 16th anniversary of her debut album Da Baddest Bitch, Trina released the single "Overnight", which discusses the ups and downs of her career including lawsuits, label issues, and being underestimated.[50] On April 1, 2016, Trina released the single "Forget That", featuring Steph Lecor, from the Meet the Blacks soundtrack.[51] On July 11, Trina participated in Missy Elliott's tribute for VH1's Hip Hop Honors: All Hail The Queens. On December 3, Trina celebrated her 38th birthday by unveiling a surprise EP, Dynasty 6, at a private Art Basel event.[52]

On August 25, 2017, it was announced that Trina and Trick Daddy would star in the VH1 reality television series Love & Hip Hop: Miami.[53]

On June 21, 2019, Trina released her much-delayed sixth studio album, The One.[54]

Trina started the Diamond Doll Foundation, a non-profit organization that helps younger girls with their life struggles.[60] The organization is partnered with the Florida Entertainment Summit to organize the Jingle Bell Toy Drive for children in South Florida.[61][62][63]