Jen Cass was born in suburban Detroit and grew up on a steady diet of Motown, as well as folk and pop from her parents' record collection. By the early '90s, Cass was writing and performing her own songs throughout the metro Detroit folk/coffeehouse scene. She eventually relocated to the Pacific Northwest, where in 1996 she self-released her debut album. Recorded with the help of infamous Siberian surf rockers the Red Elvises, Brave Enough to Say was a warm, largely acoustic release falling somewhere between Shawn Colvin and Ani DiFranco. Cass toured throughout the U.S., selling the album as she went. Eventually, she came to the attention of John Jennings, producer and longtime instrumentalist for contemporary singer/songwriter heavyweights like Mary Chapin Carpenter, Indigo Girls, and John Gorka. Jennings took Cass under his wing, helming her next record and enlisting friends from Carpenter's band to play on it. Skies Burning Red appeared in January 2003.