Radin relocated to Los Angeles and aligned himself with the Hotel Cafe, a unique Hollywood venue specializing in performances by singer/songwriters. He soon found himself playing national tour dates with a number of Hotel Cafe regulars, including Ingrid Michaelson, Sara Bareilles, and Meiko. Meanwhile, he issued a pair of digital EPs while readying the release of his sophomore album, Simple Times, which arrived in late 2008. The album was released in the U.K. two years later. Meanwhile, Radin placated his American fans by issuing a short EP, Songs Under a Streetlight, and putting the finishing touches on The Rock and the Tide, which appeared in October 2010.

In 2012, Radin returned with the album Underwater, featuring musical contributions from such musicians as pianist Benmont Tench (Tom Petty), drummer Jim Keltner (Bob Dylan), and others. Another studio effort, Wax Wings, appeared the following year. Radin then delivered his sixth studio album, 2015's Onward & Sideways, which featured a guest appearance by Sheryl Crow. He returned with The Fall in 2017. His first album produced completely on his own, The Fall included the single "High and Low." ~ Marisa Brown & Andrew Leahey