Sam Outlaw had a successful advertising career in Southern California; however, on his thirtieth birthday he experienced what he calls "an existential crisis moment" and realized that only music has ever made him feel anything. He immediately switched gears to pursue his passion. Sam Outlaw self-released an EP in 2014. It immediately created a buzz and he secured performance slots at the Stagecoach Festival and AmericanaFest produced by the Americana Music Association. He landed his music video on CMT. Outlaw caught the attention of Ry Cooder who asked to produce and play on Outlaw's first full length album. Recorded, mixed, and engineered in North Hollywood, he enlisted a crack group of backing musicians to record "Angeleno", including Bo Koster (My Morning Jacket), Taylor Goldsmith (Dawes), Gabe Witcher (Punch Brothers) and vocalist Arnold McCuller.