Thomas was first a dancer for Damian Dame. In 1991 she joined the group TLC, replacing founding member Crystal Jones after Tionne Watkins and Lisa Lopes found it was necessary to replace her. Soon after meeting Watkins and Lopes she was nicknamedChilli so that the group could keep the name TLC. Through their four studio albums and numerous singles, TLC went on to sell over 45 million records worldwide and solidify themselves as one of the best selling girl groups of all-time. Their last album 3D, was released in November 2002, seven months after the death of bandmate Lisa "Left Eye" Lopes. In 1995, and again in 2003, she was voted one of People magazine's "The 50 Most Beautiful People".
In 2006 Thomas was rumored to have signed a four-album deal with Akon's Interscope Records label Kon Live Distribution, which will release solo debut album was to be released in Fall 2007. On August 31, Chilli has confirmed that she is not signed with Akon and she is currently unsigned but looking over a few label offers. The album will still include work done with executive producer Missy Elliott as well as tracks produced by Timbaland, Dallas Austin and Will.i.am. Some of the songs have already been leaked on the Internet. A track titled "Gameproof", featuring T-Boz was leaked in Spring 2006. On February 16, 2007, "Straight Jack", a track featuring Missy Elliott produced by Polow Da Don, was leaked but will not be featured on her debut album. The song's composition is now used by Nicole Scherzinger's first single, "Whatever U Like". Chilli both sings and raps on the leaked tracks. "Straight Jack" recently entered the Deutsche Black Chart in at #35. The former first single, "Glidin'" leaked on the internet May 15, 2007. The first single later became Gameproof.
Chilli recently confirmed in an interview that Point of View is not the name of her album, and it was simply made up.
In a recent interview from CyberTLCWorld, she asked fans to request Gameproof (feat. T-Boz).