Outlaw

Country-rapper Outlaw cultivated a large online fan base through his comedic videos for YouTube, a popularity he spun off into merchandise, branded dipping tobacco, and eventually a recording career. Born in Sarasota, Florida on May 25, 1991, Jared Outlaw spent some time working as a fisherman in Alaska before setting up shop in the lower 48. Soon, he was making "vidjas" on YouTube, starting his channel in 2007. Over the next decade, he acquired fans through his backwoods comedy, which eventually morphed into parody songs. His first digital singles -- 2012's "Dip Time," 2013's "Backwoods Badass" and "She Looks Better After Every Beer," 2015's Hank Jr. parody "Yuppie Folks Can't Survive," 2016's Jon Pardi parody "Sag in Her Boobs" -- all veered toward comedy, but his 2018 album, Backwoods Badass, pushed him closer toward straight-ahead hick-hop. ~ Stephen Thomas Erlewine