In March 2016, Simpson released the first track from his third album, "A Sailor's Guide To Earth", a song called "Brace For Impact (Live a Little)", with the album itself released in April. The album, which was recorded live, has been described as a "heartfelt" guide to living from Simpson to his infant son, and Simpson produced it himself, replacing Dave Cobb, the producer of his two previous records. It features work by The Dap-Kings from Brooklyn's Daptone Records, as well as a cover of Nirvana's "In Bloom." "Sailor's Guide", which marked Simpson's major label debut, was nominated for Album of the Year and won Best Country Album at the 59th Grammy Awards. In January 2017, Simpson appeared on the Felicity Jones-hosted episode of "Saturday Night Live", playing "Keep It Between the Lines" and "Call to Arms."