In 1980 he met singer-songwriter Buddy Miller. He played in Miller's band in the active twang music scene that was evolving at the time. During his time in New York City, he also worked in the mailroom and as a messenger at Rolling Stone magazine. He often was assigned to pick up and drop off photographer Annie Leibovitz's equipment. Lauderdale joined the national touring production of Pump Boys & Dinettes, which eventually reached Los Angeles where he met musicians Rosie Flores, Billy Bremmer, Pete Anderson, Lucinda Williams, Dale Watson, and others. John Ciambotti became Lauderdale's manager and Lauderdale relocated to Los Angeles in the late 1980s, recording an album for CBS (which was later released as The Point of No Return). The record was influenced by the Bakersfield sound of Buck Owens. Armed with a catalog of a few hundred songs he had written, Lauderdale was able to get a publishing deal with a small company called Blue Water Music (based in Houston, with a small office in Nashville). Living in Los Angeles he made a record with Anderson producing, but it was never released. Lauderdale then got a publishing deal with Reprise and moved into the second floor of Buddy and Julie Miller's house until he got his own place in Nashville. In 2013, Lauderdale started his own record label, Sky Crunch, so that he could release his many albums on a schedule that suited him. In April 2018, Lauderdale signed to Yep Roc Records. Solo career Lauderdale's solo debut, Planet of Love, was produced by Rodney Crowell and John Leventhal and released in 1991. Lost in the Lonesome Pines, a 2002 collaboration with Ralph Stanley, won the Grammy Award for Best Bluegrass Album. The Bluegrass Diaries won the same award in 2008. In 2003, Lauderdale was joined by roots/jam band Donna the Buffalo on the album Wait 'Til Spring. Could We Get Any Closer? was nominated for a Grammy in 2009. In 2013, Lauderdale released Old Time Angels (a bluegrass album) and his first solo acoustic album, Blue Moon Junction, followed by Black Roses, with the North Mississippi All-Stars. Lauderdale appears on Laura Cantrell's 2013 release No Way There From Here. 2014 saw the release of his album I'm A Song. Lauderdale will release his new album Time Flies on August 3, 2018, along with Jim Lauderdale and Roland White. Collaborations In 2007, he began a collaboration with