A Musical Tribute to the Last of the Great Toadstool Madonnas (1974) (Gary Apple) This self-produced and self-released debut album includes original material in a variety of styles. Recorded in Independence, Missouri and mixed and mastered in L. A., this album was released only on vinyl and only in the Kansas City area. It received a glowing review by music critic Robert Butler (in the Kansas City Star), got significant airplay on local rock station KUDL-FM, and sold well. Copies are occasionally available on eBay, but generally hard to find.
The First One’s Free (1978) (Gary Apple) Recorded for and released by Monument Records on vinyl, cassette, and 8 track, numerous tracks from this album received significant airplay. The second single released (“Shoot ‘em Up, Cowboy”) was headed for top 40 success when misfortune intervened. Monument lost its distribution deal with Phonogram and promotion and distribution came to a sudden halt. Copies can usually be purchased on eBay and can occasionally be found in second-hand record stores.
Sessions (2001) includes selections from three different recording sessions using three different rhythm sections. The first session was recorded in Los Angeles (1980) with members of "Snapshot" (nearly all of whom were KC ex-patriots). The sessions recorded in Kansas City (1981) featured members of “Shooting Star” and “Blue Riddim” (two of KC’s most successful bands). This album was recorded for Mad Dog Records, but the label went bankrupt before the album was completed. Winston completed the album eighteen years later (1999-2000).
Hopeless Romanatic (2001) marked Winston’s return to songwriting and recording after a lengthy hiatus. Apart from a few guest soloists, Winston played all of the instruments and sang all of the vocal parts himself. Most of the songs can be best described as coming from the rock end of the Adult Contemporary spectrum. The second word in the title is not a misspelling of the word “Romantic” – it is a combination of the words “romantic” and “lunatic.” Winston’s take on the condition a romantic may take on after falling in and out of love a few times.
The Toadstool Madonna Is Free (2003) is an anthology that includes four songs from "A Musical Tribute to the Last of the Great Toadstool Madonnas,” plus all ten songs from "The First One's Free" - and three unreleased tracks recorded at the same time as "Hopeless Romanatic." As usual Winston covers a variety of musical styles.
Lessons in the Art of Loving (2004) Eighteen tracks. Fifteen new songs by Winston Apple and the first cover songs he ever recorded: a reggae version of "Imagine," a ska version of "When A Man Loves A Woman," and a reggae-influenced, R&B version of "Louie Louie."
Hot Little Love Monkeys/Masters of Terror (2008). The lyrics to the songs that make up the “Masters of Terror” section of this CD form a conceptual mini-album within the larger CD, dealing with issues related to the War on Terror and the war in Iraq. The music on these tracks include a variety of musical styles - rock, folk-rock, a ballad, gospel/reggae, and electronica.
Hearts on the Line (2008) All of the songs on this album deal with love, and with love gone wrong. Most of the songs on the first half of the album are bluesy, piano-based pop-rock, with a few interesting detours.
Alias Zimmerman! (Apple Sings Dylan) (Double CD - 2010) A double album (26 songs) of classic Bob Dylan tunes from early in his career. Winston’s versions are recorded with a full rock band, with a variety of influences: pop, reggae, blues, folk, country.
Amusing Ourselves to Death (2011) With the inclusion of a 12-panel, poster fold lyric sheet, the songs on this album come wrapped in a very attractive package that make owning a physical copy of the album a desirable alternative for those not wedded to individual song downloads. Settle into a comfy chair with the lyric sheet in hand and listen to this album from start to finish. You will be amused, but it won't kill you.
“A” is for Apple (2011) (as “Pa Apple”) – Children’s album. A mix of originals and cover songs.
The Cover Song Collection (2012) Winston left the songwriting to others in this compilation of 21 of his favorite songs by other writers and artists. Most of the songs are from the 50s, 60s and 70s, some of the arrangements stick fairly close to the original recordings, others venture boldly into new versions that are quite distinct from the originals. With 21 songs on 19 tracks (including a 3-song medley of songs by The Drifters) done like you've never heard them before, you can simultaneously take a stroll down Memory Lane and venture boldly into new musical terrain.
Radio Bay USA (2013) Reggae and ska versions of some classic rock, country-rock, and rhythm and blues hits from the fifties, sixties, and seventies. All cover songs.
The Two Tones (2013) Winston wrote all of the songs. Ska and reggae, with pop and rock influences and production values.
Allow Me to Demonstrate (2015) The songs on this album show a strong influence mixing Bob Dylan's early work with a bit of Woody Guthrie thrown in for good measure. The stripped-down versions were slightly more complex recordings of the type Winston typically does prior to recording full versions with other musicians and were originally intended to be the final versions of these songs. Over the next few years, however, Winston did record full band versions, which are sprinkled throughout his next three albums.
We Are Glory Bound (2017) Full band versions of seven of the songs from “Allow Me to Demonstrate.”
Save the Humans (2018) includes songs written by Winston between 2014 and 2018 with a common lyrical theme. All of the lyrics address threats to the well-being and continued existence of the human race, refugees, or victims of gun violence.
The Ones with Horns (2019) includes full band versions of songs Winston wrote between 2014 and 2018. There is a four-piece horn section on every track (hence the title). Most of the songs fall within the reggae-ska genre. The lyrics are overtly political.