Shaggy emerged in the early ’90s as the biggest crossover success in dancehall reggae. Not only did he become the genre’s most commercially potent artist in the international market, he managed to sustain a lasting career over the coming decade thanks to wildly popular albums like 1995’s breakout Boombastic (featuring the chart-topping singe of the same name) and 2000’s multi-platinum Hot Shot. Perhaps in part because he wasn’t based in Jamaica, he never really needed to have it both ways; virtually ignoring the hardcore dancehall crowd, Shaggy’s music was initially geared toward good times, a friendly (if horny) persona, and catchy party anthems. While he wasn’t shy about lifting hooks wholesale from pop hits of the past, he also had fairly eclectic tastes, giving his records a musical variety lacking from other dancehall stars. As a result, Shaggy became one of the scant few reggae artists to top the album and pop singles charts in America, not to mention numerous other countries where he’s had even greater success. His approach seemed to work and he remained both busy and relevant heading into the next decade, landing another major hit with “Church Heathen” from his 2009 album Intoxication and continuing to nurture his collaborative spirit, recording with friends like Rayvon and RikRok as well as releasing an album with the legendary Sly & Robbie in 2013’s Out of Many, One Music. In another unusual crossover, he collaborated with Sting on the 2018 duo album 44/876, before returning to solo work with 2019’s Wah Gwaan?!