Alan Singley is bummed. Or at least that's what the local songwriter—one of my favorites—told me in a recent email. Naturally, I was concerned. But I was also excited to hear his sad new material, as I've always gravitated toward Singley's more introspective songs (he ranges in topic from cats to absent fathers, in sound from Bacharach-esque melodrama to Phil Spectorish psych-wonder). I figured I'd better check in.

When I found the 25-year-old Florida native outside his Southeast Portland home (which he shares with Kind of Like Spitting's Ben Barnett, producer extraordinaire/Point Juncture, WA member Skyler Norwood and pianist Tyler Evans), he seemed happy as ever. And he admitted, "After I sent that email, everything got better." Singley credits the shift largely to the sonic realization of his "first fancy, fancy arrangement [with] horns and viola." But even in rough, piano-only form, the loungy material he played for me that evening is all the better for his short-lived melancholy.

The quirky songwriter's recent strife was breakup related, but—seated at Evans' piano with a dry-erase board of new songs and his cat, Joon, lounging on a nearby blanket—Singley claims to be "over it." But on new songs like "We'll Become Sand," which will appear on Singley and band's upcoming Feeling Citrus (out this spring), he sounds pretty darn morbid, singing, "The sky is blue/ Soon it will be gray/ All will vanish someday." He says it's all part of a coping mechanism: "I think the best way to deal with any problem is just to remember we're all gonna die," he explains. "I like to write more universally so everybody can relate...and, really, [songs about her] are and always were a gift to her, and I'm not an un-gifter. I'm excited to express it to whoever wants to listen."

Part of what Singley thinks will make people want to listen is his new, über-orchestrated approach—which takes advantage of his coworkers at Ethos Music Center, where Singley teaches elementary-age children to play everything from folk traditionals to Johnny Cash songs. And he's got it all mapped out: He sings faux accompaniments along to his piano; he calls out time-signature and key changes with glee. Does he tell his players what he wants something to sound like? "No! I don't just tell them," he says, breaking out a book of flute and violin parts he's handwritten in pencil. Singley is realizing a dream: "There's, like, 800,000 bands in Portland," he explains, "and I've always wanted to be the band that has the orchestra. But not, you know, 'I kinda want you to do this.' It's written out. 'Play this.' We're tight."

Digging into his craft has not only yielded awesome arrangements-to-be, it's also helped Singley cope: "Writing songs makes me proud of myself and pulls me out of a good depression," he says. "But no one wants to listen to a privileged white American hipster boy complain." Sorry to break it to you, Alan, but if you keep cranking out songs like these, people certainly will.

Listen to Singley's at-home performance here:



Singley plays solo Wednesday, Nov. 28, at Pix Pâtisserie-Hawthorne. 8 pm. Free. All ages. Alan Singley & Pants Machine plays Thursday, Nov. 29, with Chores and Bark, Hide and Horn at Holocene. 9 pm. $8. 21+.