Winston began his musical career singing and playing drums in Kansas City area rock bands. As his interest in songwriting began to develop, he switched to keyboards and then learned to "bang out a few chords" on guitar as well.

After years of playing in bars, at frat parties and school dances, Winston was offered a management position at Cavern Sound Recording. In addition to his managerial duties, he worked as engineer on numerous projects. During this period, he took full advantage of the primary perk associated with his position - free use of the studio when it wasn't booked.

His first album, A Musical Tribute to the Last of the Great Toadstool Madonnas, was recorded at Cavern 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.

The success of his initial recording effort led Apple to focus most of his time and energy on songwriting and recording. Several of the songs he wrote during this period were picked up by major publishers (Famous Music, Owepar, and Combine).

During the summer of 1977, Apple went to Nashville to produce master recordings of several of his songs. With Chuck Lackner playing matchmaker, the recordings were brought to the attention of Fred Foster, which led to a contract with Monument Records. Apple's second album The First One's Free, released on Monument, 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.

As Monument continued to seek a new distributor, Winston remained under contract to both Monument Records and music publisher Combine Music. He continued to write, but was eager to get back into the studio. With Monument's permission, he recorded 11 songs 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.

During the summer of 2000, Winston recorded a new album and completed the Mad Dog recordings. 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 from The 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 has 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 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 ("A Is For Apple") 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 this year, 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 new album ("Amusing Ourselves To Death") entertaining as well as thought-provoking. Most of the tracks are also extremely danceable, with strong grooves.

Check it out. You will be amused and inspired. And it won't kill you. We promise.

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