Winston Apple looks back on 40 years of songwriting

“Hearts on the Line” by Winston Apple, from Hearts on the Line (Speakeasy Productions):

The words true, love and heart appear in virtually all of the 15 tracks on Winston Apple‘s new album, Hearts on the Line, and not one of them is about his current wife.

“I also have three divorces to pull from,” says the 59-year-old singer-songwriter, whose round cheeks are kind of, well, apple-y. We’re in his plush living-room studio in Independence, which is rigged so that he can record without disturbing his sleeping wife if inspiration strikes.

“I keep telling her that if she wants me to write songs about her, we’d have to break up,” Apple says. “I’ve written about one and a half love songs my entire career.”

Indeed, the majority of the love stories in Apple’s songs are sour: Lovers rejecting each other, growing apart, giving up. Representing many years of botched romances, Hearts on the Line is a mixed bag of songs Apple wrote in the 1970s and songs he wrote last fall. Most of the sentimental tales are delivered in an Americana vein that brings to mind the smooth country rock of the Eagles and the earnest bounce of Randy Newman.

Saturday, June 7, at Bar Natasha, Apple and his band celebrate the release of Hearts on the Line and his other new album, Hot Little Love Monkeys/Masters of Terror. The latter is kind of like an LP that Apple splits with himself. The first few songs are more love-related stories that fit under the Hot Little Love Monkeys theme; the rest represent Apple’s response to the war in Iraq and post-9/11 life in America. Apple says he could have filled up two more CDs. “I have 20 to 30 songs still ready to record,” he says. “They’re all my children, and they all deserve to have something done with them.”

“Prolific” doesn’t quite describe the unsigned baby boomer.

A retired teacher — he taught social studies at Van Horn High School, his alma mater, for 21 years — Apple also self-published a book on public education in 2003. He’s now working on a volume of political essays. “I love trying to figure out what’s wrong and what we should be doing different,” he says. “It helps me figure out who to vote for.”

His Libertarian philosophy underpins another one of his projects, Workfareinc .org, a “Bono Jr. kind of thing” through which Apple hopes to employ people to build inner-city townhomes and plant trees in rural areas. All of the balls he’s juggling fit with the “project-oriented lifestyle” that he imagined for himself as a younger man.

“I never believed that I would last at anything that long,” Apple says.

He was wrong about that when it came to music.

“I came perilously close to realizing my lifelong ambition of being a one-hit wonder,” Apple recalls. In 1978, he released an album on Nashville’s Monument Records — onetime home of Roy Orbison and Kris Kristofferson. Apple’s hit would have been a song called “Shoot ‘Em Up, Cowboy” if Monument hadn’t lost its distribution deal four months after the album’s release.

Apple moved back to the Kansas City area, but he continued writing songs that he hoped to record for Monument for the remainder of his five-year contract. That never happened. And a subsequent record label he got involved with — Mad Dog Records — also ran into financial trouble.

Eventually, Apple realized that he should find a more dependable means of paying the bills. “It reached a point where I had to sell my piano one month to pay rent,” Apple says. “I took that as a sign.” So he called the Kansas City, Missouri, School District to put his teaching degree to use.

It was supposed to be a break from music. But looking back, Apple realizes that, almost unconsciously, he never stopped making up songs. “I sang a lot, for a social studies teacher,” he says.

At least two of the songs from his teaching days made it onto Hot Little Love Monkeys. “Loneva” was inspired by a female student of Apple’s. “All the boys were just crazy about her,” he says. Bonus track “I Like Snickers” is Apple’s one and only rap, a favorite among his students, who took to calling him Ap Doggy Dog and begging for spontaneous hallway performances of the farcical rhyme.

“Now, that’s probably the closest thing I’ve had to a hit song,” Apple concedes.

Well, this decade, anyway.