In the spring of 2013, Simons released his second full-length album Beautiful Pain on Best Revenge Records.[2] The album was co-produced with Mikal Blue and mastered by Gavin Lurssen of Lurssen Mastering. It includes songs Simons co-wrote with Jason Mraz, Jason Reeves, Glen Phillips, Mikal Blue, and others. With the exception of drums, which are played by Robin DiMaggio, the United Nations' musical directo, all instruments on Beautiful Pain were played by Simons.
Additional featured artists on the record include Alex Al (bass), Lenny Castro (percussion), Zac Rae (keys), Tyler Hilton (piano, vocals), Tower of Power's Bill Churchville (trumpet, trombone), and Sean Hill (saxophone). Simons' debut EP Currently was released on Maverick Records in 2004 and his debut Can You Hear Me, a full-length album, was released on CBS Records in 2008. He toured nationally and internationally, opening for Coldplay, Train, Guster, and REO Speedwagon amongst others. He has also worked as a writer, musical director, singer, bassist, and guitarist with notable acts like Chris Cornell, Gnarls Barkley, Snoop Dogg, Josh Kelley, and Tre Hardson.
In 2011, Simons appeared on VH1's Celebrity Rehab with Dr. Drew alongside his stepfather, actor Eric Roberts, who was a patient. A performance of his song “Unstoppable” on the show had over 10,000 iTunes downloads in only two days.