The Outlaw Country Cruise marked its fifth installment with one of its strongest lineups yet — so strong, in fact, that it made choosing between artists with conflicting set times nearly impossible. Fortunately, many of the singers, songwriters, and musicians played multiple times and popped up on one another’s stages. Steve Earle, in particular, was seemingly everywhere: leading a bon voyage photo op and teaching a songwriting class one moment, and singing with his band the Dukes and in put-together collaborations, the next. As Outlaw Cruisers already look ahead to next year’s sailing — January 21st through 27th, 2021 — we shout out the 10 highlights of 2020’s rowdy journey to Key West and Jamaica.