Thomas began working on her solo album in 2000 after the completion of promotion for TLC's third album, Fan Mail (1999).
In 2000, she was featured in the made-for-television movies A Diva's Christmas Carol, Love Song (with Monica), and in the film Snow Day.
In 2001, she co-starred in the action film Ticker, directed by Albert Pyun and "House Party 3".
The series, What Chilli Wants, which documents Thomas's quest to find love and manage her life with the help of love and relationship expert Tionna Tee Smalls, premiered on April 11, 2010.
At age 20 Thomas became pregnant by producer Dallas Austin, however due to career aspirations and the outside pressures, she aborted the pregnancy.
For the music video of the song, “Ain’t 2 Proud 2 Beg” Thomas and other band members wore condoms on their clothing.
In 2003, Thomas and Watkins teamed up with Agouron Pharmaceuticals to create a national education program about HIV/AIDS.
In 1991, she joined TLC, replacing founding member Crystal Jones, and was nicknamed "Chilli" by Lisa Lopes so that the group could retain the name TLC.
The group went on to sell over 65 million records worldwide and became the second best selling group in the world and first in the US girl groups of all-time.
The album was once rumored to include work by Missy Elliott as well as tracks produced by T-Pain and Tricky Stewart.
Certain tracks that were intended for the album were leaked from 2006 to 2008.
The program supplied people with information about what the disease is, medications to help with the disease, and treatment for the disease.