According to an interview in 2002 by Brian Keyo and to the liner notes for Samuels CD "Ska Authentic," Winston started recording for Clement "Coxson" Dodd in 1961. His first release was "In Jail" on the All Stars label. His followup song was "In Paradise," also done for producer Dodd. He then recorded "Angela" for producers Nembhard & Henry's N & H label. That was a #1 hit. In 1964, Samuels began recording for L. O. Pottinger's SEP label. Among his hits for Mr. Pottinger were "Be Prepared," "You Are The One" and "Come What May."
Samuels also cut hits for other producers such as Lloyd "Matador" Daley and Cecil "Prince Buster" Campbell. For Matador there was "Here I Come Again" and "Give To Get." For Prince Buster there's "Peace Of Mind," "Holding Out" and "I'm Still Here." After emigrating to the US, Samuels recorded for the Clintones label in New York City in the 1970s. "Let's Get It On" and "Lick It Forward" are two of those. A 16 track compilation of his 1960s recordings titled "Ska Authentic" was released in 2000. It's distributed by Rainbow Records, 4124 NW 21st Street, Lauderhill Florida 33313. Samuels was part of the Legends of Ska concerts in 2002 and movie in 2014.