Although the freestyle has been quite popular in New York and Miami, Timmy T was one of the most successful singers in freestyle that came from California.
Timmy T started out in the 1980s in small rap groups in Fresno, but felt that he would rather do dance music. He purchased a Moog synthesizer and a Roland TR-808 drum machine at a pawn shop, and recorded his first single, "Time After Time", in his garage. After getting that single pressed on vinyl, he rode his motorcycle to a local Fresno radio station to ask them to play his song. After the DJ played the song, there were many calls requesting who was performing that song. The DJ recommended that Timmy T take his record to radio stations in Los Angeles for more exposure. After Los Angeles pop station Power 106 played the record, it received airplay from several more stations throughout the country including Hot 97 in New York. Timmy got a record deal with Quality Records, and "Time After Time" went on to peak at #40 on the Billboard Hot 100 singles chart. He released another single at the end of 1990, the ballad "One More Try", which proved to be much more successful than his first single, selling over a million copies and climbing to the top of the Billboard charts the following year. The success of the single drove the album, also named "Time After Time," to the #46 spot on the Billboard 200 albums chart.
He recorded his first album Time After Time, featuring the title track (his first single), "What Will I Do", "One More Try", and "Over and Over". One of the singles from his second album, All For Love, reached the charts, however his song "Over You" was featured in the motion picture The Raffle in the company of Elton John. The other singles of the second album was "Cry a Million Tears" and a cover of the song originally by Eric Carmen "Boats Against the Corrent". None of these singles entered the chart music of any country, but the song "Over You" gained some prominence by entering the soundtrack of a movie called "The Raffle". A year after the release of his second album, he distanced himself from the spotlight to focus on the birth of his son.
Today, Timmy T still performs along with other freestyle acts from the late 80s and early 90s. He is still active in putting together these shows for people who still enjoy the freestyle era.