 Nyora kuenderera mberi kweiyi ndima - Muna Kurume 2016, Simpson akaburitsa rwiyo rwekutanga kubva mualbum yake yechitatu, A Sailors Guide To Earth, rwiyo runonzi Brace For Impact Rarama Zvishoma, nealbum yacho pachayo yakaburitswa muna Kubvumbi. Iyo album, iyo yakanyorwa mhenyu, yakatsanangurwa se mwoyo mutungamiri wekurarama kubva kuna Simpson kuenda kumwanakomana wake mucheche, uye Simpson akaigadzira iye pachake, achitsiva Dave Cobb, mugadziri wezvinyorwa zvake zviviri zvakapfuura. Inoratidzira basa neDap-Kings kubva kuBrooklyns Daptone Records, pamwe nekutenderera kweNirvanas In Bloom. Sailors Guide, iyo yakaratidza kutanga kwaSimpson kwekutanga, yakasarudzwa kuAlbum yeGore uye yakakunda Best Country Album pa 59th Grammy Awards. Muna Ndira 2017, Simpson akaonekwa paFelicity Jones-yakagadzirirwa episode ye Mugovera Manheru Live, achitamba Ramba Icho Pakati Pemitsara uye Kudaidzira Kune Zvombo. 