After placing ninth on American Idol's first season, Jim Verraros moved to Los Angeles, where he was cast in the LGBT independent comedy film Eating Out. Around the same time, he connected with Gabe Lopez, a singer-songwriter and music producer based in that area. Lopez had heard American Idol: Greatest Moments, a compilation album that Verraros had been featured on, and wanted to begin a collaboration. The two of them worked out of Lopez's home studio. A demo album resulted, titled Unsaid and Understood, which Verraros and Lopez self-released in 2003.
As the first, and at that point, only American Idol finalist to be out publicly, Verraros had already been the recipient of significant media attention from the LGBT press; Out magazine had named him as one of "2002's Most Intriguing People". When Unsaid and Understood was released, The Advocate's Adam B. Vary named it as one of his favorite new indie albums in the LGBT music scene. Individual songs from Unsaid and Understood topped's Rock and Pop charts, and one of the album's songs, "I Want You", was featured on Bi the People, a 2003 compilation album of "bisexual artists and friends", which was released to raise money for the Bisexual Foundation. Unsaid and Understood won the 2004 Out Music Award for Outstanding New Recording – Debut Male and was supported through a tour of gay clubs.
Despite the traction that Verraros was gaining within the LGBT community – the Chicago Sun-Times called him a "gay icon" in 2004 – he was unable to convince any major labels, either in the United States or in the United Kingdom, to release Unsaid and Understood. Struggling financially, Verraros continued working at a tanning salon, where he had found employment shortly after moving to LA. Over the summer of 2004, he learned that Koch Records, an indie label based out of New York, was preparing a compilation album of music by American Idol finalists. Koch Records wanted to know whether Verraros had anything to contribute to the planned album, and Verraros sent in a demo tape. He received a record deal within a week.
Unsaid and Understood was then retooled as Rollercoaster. Several of the same songs are featured on both albums, although Rollercoaster also features new material.