For songwriter Luke Winslow-King, 2014-2015 was the kind of year that nobody would ever want to live through. Never much of an outlaw type, he spent a few weeks in solitary confinement as the result of a low-level pot charge. He got out of jail and found himself at the start of a long and painful divorce. If you’re supposed to suffer to sing the blues, Winslow-King got his suffering out of the way in one go.
The product of that year is his new album, I’m Glad Trouble Don’t Last Always (Bloodshot)—unlikely enough, an album more encouraging than depressive. As it turned out, the bad experiences did more than put him through the wringer: They also made him think of his priorities as an artist and what he wanted to put across. And when you’re locked up by yourself for 23 hours a day in Michigan, thinking is about all you’re able to do.
“I sat myself down and thought about it: ‘You’re going to make a breakup album, what are you going to do?’ And I didn’t want to start moaning about the bad things that happened, that’s not very constructive. But when I hear a song like (Dylan’s) ‘It’s All Over Now, Baby Blue’ or the great Donny Hathaway songs—those were the ones that helped me through the breakup and made me feel like, ‘This is the worst feeling I’ve ever had in my life but it’s going to be okay, I’m going to be running through the sunshine eventually.’ Even for the members of my audience, I wanted to offer that. ‘Here’s the story of my own heartbreak, maybe this can help somebody else get through.’ That seemed more important than coming out with a depressed or angry album.”
Until that point, most of Winslow-King’s life and career had gone rather well. Born in northern Michigan, he had musician parents who encouraged his talent from an early age. Though he grew up absorbing the same rock radio as everybody else, he had early opportunities to explore a deeper well of music. After taking some classical piano lessons, he gravitated to guitar and formed the Winslow-King Blues Band while still in his mid-teens.
“We did some Hendrix covers, some Rolling Stones and a few Chicago blues things. So I got to play some rock ’n’ roll and get some stage chops when I was young.” At sixteen he studied jazz guitar at the Interlochen Center for the Arts, also in northern Michigan. “There were students from maybe 30 countries in my graduating class. It was a whole new thing, a world of art that I hadn’t seen before. That was where I got into bebop and avantgarde jazz, but I was also part of the folk music scene in northern Michigan, playing English and Irish fiddle tunes.” Dropping out of Western Michigan University after one semester, he joined a touring group playing Woody Guthrie songs, which set him on a course for his own music: “What I heard in Woody Guthrie was the playful approach he had, and the way his writing was so colorful—it shows a way to appreciate things around you, a particularly American kind of excitement.” That tour brought him to New Orleans for the first time.
As a newcomer, however, he hadn’t learned one of the first lessons about New Orleans: Don’t go parking a car full of equipment on the corner of Ursulines and Rampart. The car predictably got stolen when the band took a pit stop at a hotel on that corner. It was a turning point for Winslow-King, though; while he was stranded in town he realized he felt like sticking around. He already had a couple of friends to call on, notably John Boutté, who he’d met at a music festival at home. “One of the first places I went to was Preservation Hall. I’d studied serious jazz in school, but to see the way they were playing it there—it felt like all my worlds had collided. Here’s music that you can sing along with and take home with you, but there’s also so much improvisation involved. I always tell people that while I was stuck here for three weeks, that was enough time to fall in love with the place.” The car got recovered—still hot-wired, so they drove it up to Canada without a key. The band finished the tour, and Winslow-King came back to town.
Though still too young to get into clubs as a patron, he played his first local show at the Neutral Ground Coffee House and plugged into the still-developing Frenchmen scene, getting a regular gig at the Apple Barrel. “Knowing someone like John Boutté really helped a lot—he was a little concerned about me being 19 years old and never living in the city before. He taught me to be safe when I went out walking at night, and really became kind of an uncle to me.” Boutté also introduced him to some musical friends like Washboard Chaz, Paul Sanchez, Mike West and Shannon Powell, all of whom he hung out and played with in the early days.
His first, self-titled album came in 2008, and over the course of three further albums he gradually evolved from a traditionally based sound to a more electric one, particularly after signing with the influential Bloodshot label three years ago. Forming a musically flexible band helped as well; the core of his band remains guitarist Roberto Luti, drummer Benji Bohannon, bassist Brennan Andes, and keyboardist Mike Lynch. And for six years there was onstage foil and co-lead singer Esther Rose, who later became his wife. “The first album was really a blend of the folk music I was into at that point, along with the classical music I had studied at school. I’d been playing in bars and on the street doing Taj Mahal songs, Mississippi John Hurt tunes.
And I’d say that the stuff I was writing was a little more ethereal, because I hadn’t really discovered my own voice yet and I didn’t know how to dig into the grit of the bluesy stuff. I was trying to make prettier sounds, but I hadn’t grown up enough and didn’t have the mileage in my voice yet.”
The rock influence isn’t new either; that just goes back to his teenage days playing bars. “To me that’s coming back to roots, it’s more the sound I did when I was younger. And I’d say the sounds I hear in New Orleans are becoming more a part of what I do, so I’m playing more electric guitar and slide. When I listen to an album like The Coming Tide (his Bloodshot debut from 2013)—that’s an album I like a lot, and we sold a lot of copies of it. But I hear the sound of my not having my voice together, not having the confidence to do that music in a way that adds something that I can be proud of. And some of that confidence came from falling on my ass a few times.”
It got kicked rather severely in November of 2014, when he was back in northern Michigan and got arrested for carrying a small amount of marijuana. Though he only spent three weeks behind bars, most of that time was in solitary confinement due to a nut allergy. For much of that time he couldn’t listen to music, much less play it. “The amount of weed I had was usually something you’d get a $50 ticket for, but it was a really conservative town and the judge threw the book at me. And because I’m deathly allergic to peanuts they put me in a solitary cell, 23 hours a day by myself. I can’t even describe what that’s like—I remember that there was a blizzard outside, which just made it more surreal. For the first five days you’re not even allowed anything to read, so the food comes three times a day. Other than that it’s just you.”
He did get to work on music halfway through the stay, but by then he’d already resolved to make some personal changes.
“While I was there I quit smoking cigarettes, quit smoking weed and drinking alcohol, so it was a big mile marker in my life. And it’s not like I was in that hardcore a prison, but it gave me time to think about my priorities: ‘Do you want to be a singer, or do you want to smoke cigarettes?’ I figured I was only going to live once, so I decided to make those changes. And it was inspiring to me that my friends and colleagues in New Orleans came together and helped get me out. After the first 10 days things started to loosen up—a friend of mine sent me some musical notation stickers so I was able to work on songs, just from what was in my head. I have a song called ‘Break Down the Walls’ that will be on my next album, that was written in jail and it came from a pretty sincere place. The other thing that happened was that after the tenth day, the commissary delivery brought me a headset and I was able to listen to the radio. I’ll tell you that ‘Mr. Bojangles’ never sounded so good.”
The breakup with his wife happened soon after his release from prison. And while divorces are necessarily personal territory, it’s a subject Winslow-King discusses openly and one that he deals with explicitly over the course of the new album. And it’s a change his audience was bound to notice, since Esther was a key part of his band and well known to his listeners.
And though it’s now a year down the line, the wound is still fresh. “I went into the jail term thinking I still had a good relationship. She was my musical partner for six years, we were married and I basically found out that she was cheating on me with a man I knew from around town—there was a lot of lying about it, and it seemed that everybody else around me knew. So, to be with someone every day and then to find out something like that? My first reaction was to do things that were a lot more destructive, but I sat down and calmed myself, and thought about what would be a more constructive way to deal. I’ve always tried to be honest and raw about what I was singing, but I’d never been hurt this bad before. I’d never had something so serious and so terrible happen that I had to write songs about it. In the past I’ve made up a lot and told other peoples’ stories—which is fine, a lot of great writers do that. But for this one I didn’t have to wear anybody else’s shoes. When you write a song you either get to be yourself or somebody else, and I’m not very good at acting.”
The song “Esther Please” was written early in the sequence, and is one of the album’s more tender tunes. But his being willing to go there—to put her name directly in a song title—set the tone for the kind of album he wanted to make. “I did think about trying to protect her and hide her identity. But you know, she never apologized—she actually called me on the phone, the only time I’ve spoken to her in the past year and a half, and said, ‘Don’t write any songs about me.’ It wasn’t a vendetta but I thought that was a great title for a song, and audiences seem to like it too. And look at how many songs there are with a woman’s name in the title.”
Comparisons with classic breakup albums like Dylan’s Blood On the Tracks and Richard and Linda Thompson’s Shoot Out the Lights are inevitable (Winslow-King says he’s a fan of the former but doesn’t really know the latter). But neither of those albums was a raw outburst, and his isn’t either: Even his most messed-up times found his craftsman’s instincts intact. Consider “Louisiana Blues,” which briefly considers the possibility of blowing away his rival. “That’s actually a song I wrote a long time ago, but I reworked it for this album. It was deeply inspired by Howlin’ Wolf’s ’44 Blues’—I originally wanted to write about gun violence in Louisiana and how it’s gone on for so long, but the story changed as it went along.” Likewise, “Watch Me Go”—emotionally one of the album’s bottoming-out points—takes the soul-baring of classic R&B as its template.
“That was inspired by Aretha Franklin’s ‘I Never Loved a Man the Way I Love You’—the feeling of the piano and the Wurlitzer working together and the power-waltz feel—it’s not quite a doo-wop, six-eight thing but it almost makes you want to waltz in classic German style. Lyrically, that song is me wondering if we can still get back together; it came from one of those uncertain times in the breakup. Writing these songs kind of broke down a barrier for me—now I realize how personal my writing can be. Maybe in the future I’ll have that as a bar to set.”
Of course, the danger of writing a breakup album is that if it catches on, you’ll wind up having to relive it for the rest of your career. “I’m fine with that. I’ve been through breakups before and written love songs for people I’m not in love with anymore; there were dozens for Esther. Now I have to sing them for someone else’s love, or for the idea of universal love. Doing the album, I feel I’ve been able to let go of a lot of anger and resentment and had to find that closure within myself. And the last song is ‘No More Crying Today,’ so now I know what it feels like to be alive. You get cut really deep, and what the pain shows is that you’re living. Even though it hurts, you have to be grateful for that understanding.”
And in listening back to the album, he came up with the most unexpected epiphany of all. “Being from Michigan, I always hated Bob Seger. But now I can hear ‘Against the Wind’ and hear that line, ‘Wish I didn’t know now what I didn’t know then.’ That’s a pretty powerful line, and now I understand what it means.”