Bailey had worked on U-Roy's King Sturgav Hi-Fi sound system and was taken to King Jammy's studio in Waterhouse by Josey Wales.[4] He started a string of hits with a duet with Chaka Demus, "One Scotch, One Bourbon, One Beer",[2] which was followed by "Politician" (based on Larry Marshall's 1969 hit "Throw Me Corn"), "Chatty Chatty Mouth", "Ballot Box" (with Josey Wales) and, in 1987, the slack "Punaany" (with a lyric that included "Gimme Punaany, Want punaany, Any punaany is the same punaany"), which was initially banned from radio play until it was re-recorded with a less offensive lyric, retitled "Healthy Body".[4] His debut album, Kill Them With It, was released in 1987 and he went on to record for producers such as Papa Biggy and Donovan Germain.[2] He recorded further for Penthouse Records ("Help") in 1990 and Bobby Digital ("Ah Nuh Sin") in 1991.[2] In 1993, he began working with Jammy again.[2] In the 1990s he became known as a "clean" deejay, eschewing the slackness of many of his contemporaries.[3] He recorded with Byron Lee on some of the latter's big soca hits, and even starred in television commercials for banks.[3]