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).

A trip to Nashville to produce master recordings of several of his songs caught 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 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 was unable to provide the financing to complete the recordings, and the project was ultimately 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). Winston's latest album adds 26 songs to that total. It is 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) 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.

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