The Los Angeles four piece arrived on the music scene in 1998 with their very first show at Spaceland in Silverlake. In the audience was comedian Dave Foley who was so impressed with their performance that he introduced himself and immediately encouraged them to record some of their music. Recalls Foley of this first encounter with the fledgling Rilo Kiley:
January 1998, I was a young man, young compared to now, hanging out in L.A's alt. rock club scene. One night in particular, I found myself at Spaceland, at the bar drinking when a band started playing. They were good, so good that I stopped fighting for the attention of the bartender and turned to see who it was. On stage was a very young, delightfully unpretentious group named Rilo Kiley. Between songs they were charming, smart and funny. During songs they were brilliant. After the set I introduced myself and learned that this was their first public performance. I was astonished. They invited me back to their rehearsal space for Thai food and to hear some songs they didn't have room for in the set. Dreamily, I filled my belly with noodles and my head with one great song after another. I was in a full on, pop music fan swoon. Having decided to force myself into their lives, I suggested (insisted) that I should fund a demo recording. They relented. I also tried to talk them into changing the band's name. They were unrelenting. A lot of years have passed. I remain proud to know Rilo Kiley and grateful that I had the opportunity and ability to be of some help."
Some of the songs from that initial Foley-funded demo session formed the foundation for Rilo Kiley and the band handmade copies of the CD to sell at shows before signing to Barsuk Records and going on to release some of the most influential and acclaimed albums of the era.