At the behest of friend and fellow OctoArts recording artist, Pops Fernandez, Velasquez guested on the GMA 7 Variety TV show, 'Penthouse Live', on February 16, 1986. Martin Nievera, Pops' husband and co-host of the show, suggested to Velasquez that she drop the name "Chona" and use Regine as her screen name. That year, her father resigned from his job as a construction estimator to fully attend to his daughter's blossoming career.
Viva Records signed Velasquez to a contract in 1987, releasing her self-titled debut album Regine. The album contained the songs "Kung Maibabalik Ko Lang," "Isang Lahi, " and "Urong Sulong." Her first regularly televised performances were musical variety shows with ensemble casts, such as ABS-CBN's Triple Treat and the Sunday variety show Teen Pan Alley. Velasquez and Alley's Janno Gibbs continued to collaborate throughout the years, creating the musical Kenkoy at Rosing, recording the cover song "Magkasuyo Buong Gabi," and performing duets in concert.