Back when I was just getting into following the local music scene and realizing that there are musicians here in my own city that I could go out and see, and who I could buy CDs from directly out of suitcases at their merch tables, I came across Dan Israel's breakout album, Dan Who?

After reading about Dan in the writer Jim Walsh's column in the Pioneer Press, I immediately high-tailed it to Cheapo and picked up a copy of the record, and I fell in love with Dan's ability to convey deep emotions in a really simple way. Dan Who is an acoustic album, mostly just Dan and his guitar, and it's a story about an artist who's trying to figure out if they really want to be in it for the long haul. Is it going to be worth being so tired, and working endlessly to keep creating, keep promoting yourself, and keep putting yourself out there? Is it worth keeping that rock 'n' roll dream alive?

Almost 15 years have passed since that album came out, and that question is still at the forefront of Dan's mind. Like so many artists, he's still struggling with this idea: When do you know if the effort you've put into something is going to pay off? For my money, Dan Who? still stands up as one of the finest things he's put out, but it is rivaled by Dan, a new album that he just released this month. On Dan, we hear these same questions coming up — is this worth it? — and in this case he's not just questioning his creative pursuits, but he's also reckoning with a marriage that has come to an end. What does it all mean?

It's quite a universal theme, and something that anyone that's been through any kind of breakup can relate to, and I wanted to talk to Dan about where he's at right now, how he's feeling about the new record, and how he puts all of these really deep and profound feelings into these really beautiful, and ultimately uplifting pop songs.

The following is a condensed version of the interview, edited for length. Find the full conversation in the audio above, download it on iTunes, or find the O.K. Show podcast through Feedburner.

Andrea Swensson: When I was listening to your new record, and especially your voice, it reminds me of Dan Who? There's a beleaguered, tired, weary tone, but also a conviction. As you went back and listened to these recordings, were you aware it was coming across as a very serious album?

Dan Israel: Yeah, I think given the subject matter and the time and the emotions I was going through, it was bound to end up being that sort of album that was going to have to be sort of no-holds-barred about my emotions. Because my life was falling apart. When I did Dan Who? back in the late '90s, it's not so much necessarily the case that my life was falling apart, but I was coming face to face with a lot of conclusions, realizations that were hard to take. To compare the two things, Dan Who? was about a busted rock 'n' roll dream, and this new album is about a busted life dream. A busted happiness dream. Marriage. And in both cases, hopes crushed, dreams dashed are kind of the themes. This dream falling apart feels even more adult, somehow. It's one thing to have your career hopes dashed; it's another to have your plans for your life and your domestic life dashed. A lot of things came through the fire and are okay, especially with regard to my children, who are doing well and are really happy kids. They've adjusted really well to a kind of sudden upheaval.

In my opinion, it was kind of sudden anyway. From another perspective it might have seemed to have been evolving for a long time, but I was still surprised. I don't want to say I didn't see it coming at all, but I certainly didn't see it coming when it did happen. I thought we could work things out, and you can probably hear that a little bit on the album; there's some lyrics about how I thought we were going to work on it, but we didn't. We just didn't. For whatever reason, that's where it ended.

How long were you married?

I was married for about 16 years. In rock 'n' roll terms, that's like being married 50 years. [laughs] But the songs that I wrote for this album mostly came out of that first winter when I moved out — and if you recall how bad that winter was two years ago, that was it. So the first song on that album is called "Winter is Coming," and it's sort of funny. If I'd known how bad that winter was coming — I'm glad I didn't know how bad it was going to be. Because I felt bad enough just knowing it was going to be winter and I was going to be alone. That sort of sets the tone for the album, I guess; looking ahead to, well, ok, I'm going to be alone here now.

https://www.youtube.com/embed/M6iPCF0srDc

There's a sense of hope that comes through in the record, too. You take on a really serious topic like divorce, but you've made pop music out of it, with these upbeat melodies and rhythms. Where does that come into the songwriting process?

I do sometimes like listening to depressing, quiet, slow music, but a lot of times when I'm excited about music it still ties into that young kid in me that liked the Top 40 hit, you know? The pop hit. A lot of my love of music has to do with the pop of the late '70s, and that driving disco beat, and the fun aspect of music. So even if everything lyrically in my life is kind of down, I still want to write a hit song that's catchy and has a good beat. I have all these songs that are upbeat rock songs until you listen to what I'm singing about, and then it's like, damn. That's a bummer. But I guess I just don't think that the two things always need to line up. I tend to do these bummer tunes with the bounce — the the Wilburys bounce.

You have a real sense of humor, too.

Do I? I hope so.

Well, you named your greatest hits album Danthology. And your new album cover is hilarious.

I've had to do a lot of explaining, when people see it, if they don't know Joyce. Joyce made the worst albums list that circulated, so that's what we were parodying.

And I'm a person who loves comedy. I love Louie. Comedy often gets me out of my mental state that is bummed out. In recent years I kind of got into that show Broad City —

Yaasssssssss!

That show really cracks me up. Growing up, it was Mel Brooks, all the Jewish humor — my dad was from Brooklyn — and I grew up really attuned to Jewish comedy. So I don't really have it in me to be a comedian, but I still love comedy.

It's interesting that you mention Louis C.K., because when I reflect on my own experience with divorce, I find myself thinking about his quote that no good marriage has ever ended in divorce. So you should say you're sorry when someone tells you they are getting divorced.

Isn't that funny? That's a great quote. What are you sorry about? [laughs] I don't know what the answer is about anything right now. I'm feeling particularly lost because I'm dealing so much with health stuff, but we all have these things where we say, well, "If I could just get this figured out, I would be happy." So I've had many times in the last few years where I've been like, well if I could just feel good physically, then I'd be great. Well then I go through a little period of feeling a little better, and then it's like well, great, now it's the depression. It's like playing Whack-a-Mole with your problems. Maybe it's best to just acknowledge sometimes that if you're a certain kind of person you're probably always going to have a demon. There's going to be some demon. What are you going to mitigate those things? What are you going to do to deal with it? Are you going to create? Are you going to find a job that makes you happy? Are you going to surround yourself with people that make you happy? That's usually how I deal with things; at least when I'm dealing with them in a healthy way, and not just burying them in whatever I can put the pain at bay with.

Part of my problem is I'm just entirely too functional. And I've learned how to do everything in a way that allows me to keep doing it without quite going over the edge of the cliff. Having said that, right now, I kind of feel like I've gone over the edge of the cliff with my health, and I'm not too terribly functional right now. My body isn't really working very well right now. And I don't necessarily attribute that to drugs, but more to a life that I've tried to sustain for a really long time, and it just obviously was to some extent unsustainable.

People joke with me about it on Facebook and stuff, like "You're a machine! You're the hardest working whatever! How do you do it?" And I'm here to say, I'm not doing it. I'm here to say that any macho, oh aren't I just a tough survivor — I'm kind of embarrassed for all that bravado that I've sometimes displayed. I've put out so many albums and I'm such a survivor and I just keep going. But I'm human and I'm actually, right at this moment, as we're speaking, I'm kind of breaking down. So I need to figure out how I'm going to get healthy again.

Previously:

The O.K. Show, Episode 1: A candid discussion on mental health with Charlie Van Stee

The O.K. Show, Episode 2: Mary Beth Mueller and her one-woman crusade against cancer

The O.K. Show, Episode 3: Adam Levy’s devastating loss and beautiful new solo album

The O.K. Show, Episode 4: Irv Williams, the elder statesman of Twin Cities jazz

The O.K. Show, Episode 5: Lydia Liza on empathy, anxiety, and staying grounded in the music business

The O.K. Show, Episode 6: Hard-touring rapper Astronautalis talks about staying sane on the road

The O.K. Show, Episode 7: Mayda on her health and her journey as a Korean adoptee

The O.K. Show, Episode 8: Manchita on feminism, rapping, and her relationship with Eyedea

The O.K. Show, Episode 9: Lizzo on self-acceptance and falling in love with herself