A Charlie Brown Christmas premiered in 1965, and he bought the soundtrack album the next day featuring the music of Guaraldi. He would also watch each new Peanuts special to hear Guaraldi's newest music. In 1996, Winston released Linus and Lucy: The Music of Vince Guaraldi, primarily devoted to the theme music Guaraldi wrote for the Peanuts cartoons: fifteen television specials and one feature film, ranging from 1965 until Guaraldi’s death in 1976. "I love his melodies and his chord progressions," Winston said of Guaraldi. "He has a really personal way of doing voicings." Winston recorded a follow-up album, Love Will Come: The Music of Vince Guaraldi, Volume 2, released in February 2010. A third volume, entitled Count the Ways: The Music of Vince Guaraldi, Volume 3, released in 2021. Winston's 2002 album Night Divides the Day – The Music of the Doors consists of solo piano renditions of music by the rock band The Doors. The title of the album is a lyric from their song "Break on Through (To the Other Side)". In addition to his piano work, Winston plays 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. 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. Winston also produces recordings of Hawaiian slack-key guitarists for his own record label, Dancing Cat Records, including artists Keola Beamer, Sonny Chillingworth, Leonard Kwan, Dennis Kamakahi, Ray Kane, Cyril Pahinui, Bla Pahinui, Martin Pahinui, Ledward Kaapana, Georg Kuo, Ozzie Kotani, George Kahumoku, Jr., Moses Kahumoku, Cindy Combs, and others. He is also working on recording the American traditional musicians Sam Hinton, Rick Epping, and Curt Bouterse. 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,