[1] A native of Rochester, New York, Klein learned to play acoustic guitar and started writing songs as a college student in Kingston, Jamaica, while working on a thesis "documenting dub poets and studying the musical landscape of that country.

After independently releasing her first two albums, winning the Telluride Troubadour Songwriting Contest, and garnering several Boston Music Award nominations, she was signed to Rykodisc in 2000 by then-president George Howard.

It debuted as the number-one most-added album at triple A radio a week before its release, was given four stars by MOJO, and received a plug from the nearly 80 million readership Parade.

In 2005, Nerdcore Rapper MC Frontalot posted on his website a rap breakdown using the beat from the Jess Klein song "Soda Water".

Klein's sixth album, City Garden (five stars, MOJO Magazine) caused the Boston Globe to describe her as "Quite simply one of the most gifted performers this area has produced."