Caputo started Life of Agony in 1989 with guitarist Joey Z. and bassist Alan Robert. Drummer Sal Abruscato was recruited soon afterwards. After signing with Roadrunner Records, they debuted with the 1993 album, River Runs Red. Shortly after the release of a third album in 1997, Caputo claimed that her heart was no longer in the type of music they performed, and left the group. Caputo also guested on the track "Free Speech ", which appears on the albumMemory Rendered Visible by the band Both Worlds, released on Roadrunner Records. After leaving the group, Caputo formed Absolute Bloom, but that band broke up in July 1998. Later, she helped to re-form the Brazilian band Freax, which had broken up over ten years earlier. They developed a self-titled album in 2003. Caputo also worked extensively on a solo career in the 1990s, and released two studio albums. The original line-up of Life of Agony reunited for two sold-out shows at New York's Irving Plaza on January 3 and 4, 2003. The reunion resulted in several more shows and appearances on European festivals, as well as the recording of Broken Valley, the band's first new material since 1997. In 2003, Caputo formed a group consisting of New York musicians Mike Shaw and Dan Platt, along with Dutch musicians Jochem Van Rooijen and Jack Pisters that toured and recorded what became the album Live Monsters. In 2005, Caputo provided vocals for the song "Tired N' Lonely" on the Roadrunner United: The All-Star Sessions album. On May 1, 2006, Caputo released her third solo albumHearts Blood on Your Dawn which was only sold at her live shows, via mailorder through her website, and in the iTunes Store. In 2007, Caputo recorded her fourth solo album, A Fondness for Hometown Scars, which includes a guest appearance by Flea on trumpet, amongst others. In 2008, she toured in support of this release, with a band composed of Dutch musicians Ryan Oldcastle, Axel van Oort, and Jochem van Rooijen. The album was produced by Martyn LeNoble and was released in Europe in April 2008 by Dutch label, Suburban Records. Caputo participated as a guest singer on Dutch symphonic metal band Within Temptation's track "What Have You Done", the first single from their 2007 album The Heart of Everything. In 2011, Caputo formed a side project with Ryan Oldcastle and Michael Shaw called The Neptune Darlings, and released an album on September 15, 2011 called Chestnuts & Fireflies. The style of this CD has been called "geek rock" by The Advocate magazine.
Personal life
In July 2011 Caputo came out as transgender. For a while, her legal name was Keith Mina Caputo. "When I was Keith, I certainly wouldn't allow myself to be as flowery or as vulnerable as I do now," said Caputo in a 2016 interview that appeared on the music website No Echo. "I'm a fucking sissy, get over it ! I no longer have this masculinity or this manhood to protect. This is a transformation I've been dreaming of my entire life."