A few weeks after winning the Digicel Rising Stars competition in 2007, Virgo met Donovan Germain who produced his first hit record "Mi Caan Sleep" on the Penthouse label. Several hit singles followed, including "Wanna Go Home", "Live Mi Life", and "Alton's Medley". In June 2010, VP Records released his debut self-titled album. Virgo's 2018 album Lovesick gave him his first number one album on the Billboard Reggae Albums chart.