Oh Boy Records' A & R rep Tom Lewis caught one of these early gigs and discerned a very special talent in the singer songwriter who was still at the “tadpole stage.” Heather had made up a very rough cassette demo tape which she recorded on her Fostex 4-track. She had hoped to use the tape for booking gigs, not even beginning to consider that she might be ready for the wider world of recording contracts, national tours and TV appearances.
She signed to Oh Boy in 1993 and spent the next two years assembling her debut album MASCARA FALLS, which was overseen by Nashville producer Roger Moutenot (Yo La Tengo, Sleater-Kinney). It was a “massive learning experience.” She found it incredibly inspiring to find out how records were made and to participate in the process – hearing her songs professionally arranged and produced for the first time.
In the meantime, Heather toured the US, opening for John Prine and appearing at such illustrious venues as the Fillmore in San Francisco and the Ryman Auditorium in Nashville. She played live on NBC's "Late Night with Conan O'Brien" (still in it’s infancy) the day her debut record came out. Later, with help from Steve Martin at the Agency Group, Heather had the good fortune to open for Billy Bragg, John Hiatt, Crash Test Dummies, Jill Sobule, Ferron, Donovan, Richie Havens and Roseanne Cash, among others and even once got to appear onstage singing backup on John Prine’s “Paradise” with Prine, Tom Waits and Bonnie Raitt (two other of her musical gods). “I kept looking down at Tom Waits’ motorcycle boot stomping the stage in time and thinking, ‘is this really happening?' ”