In 1971, he switched to solo piano after hearing the stride pianists Fats Waller, Teddy Wilson and later Earl Hines, Donald Lambert and Cleo Brown.

[4] His debut album Piano Solos disappeared without much notice,[9] although it was later reissued on Windham Hill Records under the title Ballads and Blues 1972.

[5] At the request of producer Lee Mendelson in 1988, he provided the music for the TV miniseries This Is America, Charlie Brown, which Winston considered a highlight of his career.

[20] Winston suffered from a number of illnesses, and while recuperating from a bout of cancer in 2013, he played the piano in the medical center auditorium, creating 21 pieces, that he says were "kind of circular" and "minimalist".

Proceeds benefit City of Hope Hospital near Los Angeles, where he was treated and subsequently composed the musical work.

The 11-song collection includes his interpretations of music by Sam Cooke, The Doors, Stephen Stills, George and Ira Gershwin, Country Joe McDonald, among others.

[24] In July 2019, at the National Music Council's 2019 American Eagle Award Honor ceremony that recognized Vince Guaraldi, Winston performed his versions of the musician's work.

I first heard him in 1962, with "Cast Your Fate to the Wind"....And then in December 1965, I was a fan of animation, and I saw in the TV Guide that there was going to be a cartoon of the Peanuts characters, A Charlie Brown Christmas.

A lot of us remember where we were, the first time we heard "Linus and Lucy" in that special, during the dance segment.... Vince's piano just drove me crazy.

[26]In 1983, Winston started his own label, Dancing Cat Records,[5] which released his albums, with distribution by Windham Hill until the mid-2000s and subsequently by RCA.

[32] The third style he played was New Orleans R&B piano, influenced mainly by James Booker, Professor Longhair, Henry Butler, as well as Dr. John and Jon Cleary.

[34] Winston dressed unassumingly for his shows, playing in stocking feet, stating that it quieted his "hard beat pounding" left foot.

For years, the balding, bearded Winston would walk out on stage in a flannel shirt and jeans, and the audience would think he was a technician, coming to tune the nine-foot New York Steinways that are his piano of choice.

Starting with a bluesy tune inspired by Professor Longhair—Winston's most recent albums have included two Gulf Coast-inspired collections—he proceeded through seasonal favorites "Rain" (from 1982's Winter Into Spring) and "Woods" (from 1980s Autumn).

On the latter, he created remarkable 'hollowed' sounds to some notes by reaching inside the piano and muting strings with one hand while striking keys with the other.

Twenty minutes into the program, he described an unusual method of playing the piano with muted strings, a development inspired by watching blues guitar players.