When growing up, Winston\'s interest in music were instrumentals of R&B, rock, pop, and jazz genres, especially by organists. After hearing The Doors in 1967, he was inspired to start playing the organ. In 1971, he switched to solo piano after hearing stride pianists Thomas "Fats" Waller, Teddy Wilson, and later Earl Hines, Donald Lambert, and Cleo Brown.\n', '

Winston attended Stetson University in DeLand, Florida, in the 1960s, where he majored in sociology. While he did not complete his undergraduate degree, following his rise to prominence the university awarded him an honorary doctor of arts degree.\n', '

Winston was first recorded by John Fahey for Fahey\'s Takoma Records. His debut album Ballads and Blues 1972 disappeared without much notice, although it was later reissued on Winston\'s Dancing Cat Records. In 1979, William Ackerman talked with Winston about recording for Ackerman\'s new record label, Windham Hill Records. At first, Winston played some guitar pieces he liked and then some of his nighttime music on the piano. These became the basis for the record Autumn, which Ackerman produced. Autumn soon became the best-selling record in the Windham Hill catalog. Both Autumn and the following album Winter into Spring went platinum, signifying million-plus shipment in the United States. The Christmas album December became an even greater success, and it was certified triple platinum for shipment of three million. He has recorded twelve more solo piano albums. He is one of the best known performers playing contemporary instrumental music.\n', '

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