Winston's first album, A Musical Tribute to the Last of the Great Toadstool Madonnas, was recorded at Cavern Sound in Independence, Missouri and mixed at Wally Heider Recording in LA. The album was released only in the Kansas City area, but received airplay on KC area radio stations, got good reviews, and sold well.
Apple's second album The First One's Free, was released on Monument Records in May of 1978. Several songs on the album received extensive air play, particularly Shoot 'Em Up, Cowboy, which spent nine weeks on Record World's singles chart. The disc received excellent reviews and was selling well when misfortune intervened. Monument's distribution deal with Phonogram ended, and the album quickly sold out and became unavailable.
The basic tracks for Sessions were recorded in 1980 and in 1981 for Mad Dog Records. Sessions took place in both LA and Kansas City, but Mad Dog went bankrupt before the recordings were completed and the project was shelved until 2000 when Winston added new vocals and keyboard tracks and re-mixed the original tracks.
During the summer of 2000, Winston also recorded a new album. These efforts, Hopeless Romanatic and Sessions were both released on Speakeasy Records that summer.
In 2003, Speakeasy Productions issued an anthology that included all ten songs fromThe First One's Free, four songs from Toadstool Madonna, and three "bonus" tracks recorded at the same time as Hopeless Romanatic.
Lessons in the Art of Loving was recorded from April through September, 2004. It includes fifteen songs written by Apple and the first "cover" songs Winston had ever recorded: A reggae version of "Imagine." A ska version of "When A Man Loves A Woman." And a Jamaican-flavored R&B version of "Louie, Louie."
Hearts On The Line and Hot Little Love Monkey/Masters of Terror were recorded simultaneously, with the bulk of the recording done during 2007.
The lyrics to the songs that make up the “Masters of Terror” section of Hot Little Love Monkeys/Masters of Terror form a conceptual mini-album within the larger CD, dealing with issues related to the War on Terror and the war in Iraq.
The “Hot Little Love Monkeys” section of the album is also somewhat conceptual. Most of the songs include characters who could be described, with some degree of accuracy, as Hot Little Love Monkeys.
All of the songs on Hearts On The Line deal with love, and with love gone wrong. The variety (which as you may know, is the spice of life) is provided by a very eclectic range of musical styles, including ballads, rock, blues, alt country, and even a bit of ragtime.
Winston's first eight albums featured a total of three songs written by other people (cover songs). With the release of Alias Zimmerman! (Apple sings Dylan) in April of 2010, Winston added 26 songs to that total with a double album of songs written by Bob Dylan early in his career.
Alias: Zimmerman! (Apple Sings Dylan) features Dylan classics (and less well-known tunes) most of which are from the mid-sixties, re-arranged, re-interpreted, and re-imagined, filtered through Winston's unique production style: wall of sound rock, with a variety of influences: country, blues, reggae, ska, and folk.
Winston's next project ("A" Is For Apple) was another departure from his previous efforts - a children's album. Winston has provided guest vocals on several songs for Kansas City based children's entertainer Dino O'Dell. Most notably providing the voices for Grandpa O'Dell and Zar (the space alien). This experience, plus the urging of family members, convinced Winston to try his hand at entertaining the youth of America.
The resulting album consists primarily of songs written by Winston, along with a few re-worked nursery rhymes, and unique versions of "The Oompa Loompa Songs" popularized by the movie "Willie Wonka and the Chocolate Factory."
Less than a month after the release of "A" Is For Apple, Winston released his first digital single - a cover of Leonard Cohen's oft-recorded song "Hallelujah." Winston gave this powerful ballad a unique twist by giving all of the verses, except the first and last, an up-tempo, gospel-rock feel. He also over-laps the first part of each verse with the choruses.
Between February and August of 2011, Winston composed sixteen new songs, nine of which are overtly political and speak directly to events unfolding in our country and around the world. Despite the serious nature of the subject matter, Winston's trademark sense of humor is evident in enough places to make the album (Amusing Ourselves To Death) entertaining as well as thought-provoking. Most of the tracks are also extremely danceable, with strong grooves.
The Cover Song Collection (Fall 2012) is just what the title implies - a collection of cover songs recorded during 2012 and released that fall. Winston's version of Hallelujah is included along with a varied assortment of well-known and lesser-known songs, with the exception of Shout (which hues pretty close to the original version) all of the songs are significantly different from the original versions.
Radio Bay USA (released in August of 2013) is another collection of cover songs, re-arranged, in this case, with a pronounced reggae/ska influence. Several of Apple's original songs from earlier albums were also recorded as part of this project, but a burst of song-writing activity on Winston's part led to the original songs being included in a separate album (The Two Tones).
The Two Tones is both an album title (2014) and the name of Winston's new backing group. While Winston has always recorded using session musicians, the bonding that took place between Winston and the musicians performing on Radio Bay USA created a "group" mentality that led to a desire to keep the group together beyond the recording of the two albums. There are reggae and ska arrangements of six of Winston's songs from earlier albums and nine brand new songs on The Two Tones.
The songs on Allow Me To Demonstrate (2015) are both political and spiritual in nature. A strong folk influence (Woody Guthrie, early Dylan) is evident. The stripped down arrangements are a real departure for Winston and he has been performing solo more often. The lyrics really shine through with that approach and the lyrics on this album stand up very well to such scrutiny.