Born Ian Dyer, Mr. Easy immigrated with his family from Jamaica to Flatbush in Brooklyn, where he completed his education. Inspired by Dennis Brown, Dyer practiced singing along to his idol's recordings (he has also acknowledged the influence of Beres Hammond). His easygoing vocals impressed the New York-based producer Barry Dread, who took him to the recording studio. Following his experience in studio work, Mr. Easy auditioned for the famous Showtime at the Apollo. This was quite a challenge, as the Harlem audience members can be demanding in their critical approach to aspiring artists. The young vocalist survived the ordeal, winning approval from the masses. He also earned the distinction of being the first reggae singer to perform at the televised show. A notable viewer was the producer Quincy Jones, who was inspired to sign Mr. Easy for a recording contract. Signed to Jones' Qwest label, he released his debut in 1994, the well-received album Call Me Mr. Easy.
By 1995, his career was firmly established. It was at this time that Mr. Easy's manager approached Dave "Rude Boy" Kelly to produce the singer in sessions alongside the Mad House crew. This recording arrangement produced material for a projected second album. The singer also formed an allegiance with Sting International where he performed alongside Shaggy, Rayvon, and Bajja Jedd. The Sting crew toured the U.K., Japan, and the Caribbean, where they were greeted with high acclaim. On his return, Mr. Easy was recruited alongside Wayne Wonder, Frisco Kid, Spragga Benz, Alley Cat, Baby Cham, and Textra to perform as part of Kelly's Mad House crew. Since Mr. Easy's initial association with Kelly the clique had become known as Alias. The non-hierarchical group toured the U.S., where the singer enjoyed further accolades. Backed by the Kaushan Band, the artists performed as soloists and in combination while also rejecting the notion of a headline act. Notable hits with Alias included a version of the popular "Bruk Out" rhythm, "Murder," while on the "Joy Ride" rhythm Mr. Easy recorded "Funny Man" in combination with Baby Cham. The singer maintained his profile with "Rain Again," the most popular tune on the "Showtime" rhythm. In 1998, Mr. Easy embarked on sessions with Beres Hammond through the singer's Harmony House production team. In 1999 he teamed up with Hammond's nephew, Yogie, on the traditional-sounding reggae groove "You Got to Be Strong."