This is an autobiographical song about the singer's journey from her hometown of Leavenworth, Kansas, to the West Coast in search of her Hollywood dream. Etheridge attended Berklee College of Music in Boston, but dropped out to pursue her passion in California. It worked out well, as she signed with manager Bill Leopold and got the attention of various record labels, including Island Records, which gave her a deal.
"The Night Chicago Died" was written and recorded by the British group Paper Lace. They talk about Al Capone in the song, but got a lot of details wrong - understandable since they wrote it based on gangster movies.