- Winston suffered from a number of illnesses, and while recuperating from a bout of cancer, he played the piano in the medical center auditorium, creating 21 pieces, that he says were "kind of circular" and "minimalist." In 2014, he included three of the pieces in a Spring Carousel EP, and a 15-track album, called Spring Carousel - A Cancer Research Benefit released on March 31. Proceeds benefit City of Hope Hospital near Los Angeles, where he was treated and subsequently composed the musical work.
- 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 9-foot New York Steinways that are his piano of choice.
- Was considered by many music critics and experts to be the premiere, number one instrumental solo pianist in the popular music genre.
- In addition to the piano, Winston was also an accomplished harmonica and slack key guitar player.
- He launched his own label, Dancing Cat Records, in 1983, and specialized in Hawaiian music.
- Winston dressed unassumingly for his shows, playing in stocking feet, stating that it quieted his "hard beat pounding" left foot.
- After a successful bone marrow transplant for Myelodysplastic Syndrome (MDS) in 2013, he continued to record and tour while in recovery, but had been forced to postpone many of his 2023 shows due to declining health.
- "Night", his final release, featured songs popularized by Leonard Cohen, Allen Toussaint, and Laura Nyro.
- He cites the New Orleans pianists James Booker, Henry Butler, and Professor Longhair as early foundational influences.
- While on tour, Winston encouraged his audiences to bring food donations to his concerts, raised funds for the nonprofit Feeding America, and donated proceeds from shows to local food banks.
- After moving to the Bay area and signing with William Ackerman's Windham Hill label, Winston had his breakout with three platinum albums: Autumn, Winter Into Spring, and December (which went 3x platinum).
- Winston suffered from several forms of cancer, including thyroid cancer, skin cancer, and myelodysplastic syndrome, the latter of which was resolved following a bone marrow transplant in 2013.
- While many consider his work in the '80s and '90s to be largely influential in the formation of New Age music, Winston himself resisted the label, referring to his style as "Folk Piano" or "Rural Folk Piano.".
- A five-time Grammy Award nominee, Winston won Best New Age Album honors in 1996 for "Forest.".
- Winston sold more than 15 million albums.
- One of his influences was Steve Reich.
- In 2006, he recorded another benefit album, Gulf Coast Blues & Impressions: A Hurricane Relief Benefit, followed by Gulf Coast Blues & Impressions 2: A Louisiana Wetlands Benefit in 2012.
- On April 19, 2010, he appeared as the sole guest on show 575 of the multimedia WoodSongs Old-Time Radio Hour. Twenty minutes into the program, he described an unusual method of playing the piano muting the strings, a development inspired by watching blues guitar players. He can be seen reaching into the piano with his left hand and muting the strings, while with his right hand he is playing "An African in the Americas".
- In the early '70s he discovered the stride pianists Fats Waller and Teddy Wilson.
- In addition to his piano work, Winston played solo harmonica (mainly Appalachian fiddle tunes and ballads) and solo acoustic guitar (mainly Appalachian fiddle tunes and Hawaiian slack-key guitar pieces). Both his harmonica and guitar playing can be heard on his benefit album Remembrance - A Memorial Benefit, which was released shortly after the September 11 attacks.
- Later in his career, Winston recorded more tributes than original tunes. He released two albums of music by Peanuts composer Vincent Guaraldi, and in 2002 he shared an album-length tribute to the Doors called Night Divides the Day.
- Over a career spanning more than 50 years, Winston released 16 solo piano albums-including the Grammy-winning 1994 album Forest-as well as records from a number of Hawaiian slack key guitarists.
- He also donated proceeds from his 2001 album Remembrance to the families of victims of the 9/11 terrorist attacks.
- Winston partnered with actress Meryl Streep for a special LP, "The Velveteen Rabbit". He accompanied the actress' reading of children's story on piano.
- After graduating from Coral Gables Senior High School in Coral Gables, Florida, in 1967, 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.
- He is one of the best known performers playing contemporary instrumental music.
- After hearing The Doors in 1967, he was inspired to start playing the organ. In 1971, he switched to solo piano after hearing the stride pianists Thomas "Fats" Waller, Teddy Wilson, and later Earl Hines, Donald Lambert, and Cleo Brown.
- On May 3, 2019, Winston released his 15th solo piano album, Restless Wind. The eleven-song collection includes his interpretations of music by Sam Cooke, The Doors, Stephen Stills, George and Ira Gershwin, Country Joe McDonald, among others.
- Winston provided music for the TV miniseries This Is America, Charlie Brown in 1988.
- He always called his "melodic style" of play "Folk Piano" or "Rural Folk Piano." "It is melodic and not complicated in its approach, like folk guitar picking and folk songs, and has a rural sensibility," he said, adding: "Any other labels, including anything having to do with anything philosophical, or spiritual, or any beliefs, are also not accurate, as I have no interest in those subjects. I just play the songs the best I can, inspired by the seasons and the topographies and regions, and, occasionally, by sociological elements, and try to improve as a player over time.".
- Winston preferred playing in intimate venues due to his disdain for amplification.
- When growing up, his musical interests lay with instrumentals of the R&B, rock, pop, and jazz genres, especially those by organists.
- All of Winston's albums are available on his own Dancing Cat Records, with the exception of the last four releases, which came out on RCA 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.
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