There’s something joyous, even heartwarming, about hearing Freedy Johnston’s distinctive voice again. It’s been easy to lose track of him over the last decade; after all, he hasn’t released a new studio album since 2001’s Right Between the Promises , the last of his four recordings for Elektra. Between then and now he has charted a nomadic course, moving around from NYC to Austin to Madison to Nashville, with a stint in his Kansas hometown thrown in. He has messed around on occasion with a ramshackle covers band, the Know It All Boyfriends (also featuring Butch Vig and Doug Erikson of Garbage, and he has released an album of covers, an album of demos and a live recording — all while working in fits and starts on a collection of new songs that seemed (to him and his fans alike) as though it might never reach fruition. As it turns out, Rain on the City (available tomorrow) was worth the wait – in fact, it’s probably his best work since his early-’90s commercial peak with Can You Fly and This Perfect World. It’s full of his trademark finely turned phrases, and pop-rock tunes like first single “Don’t Fall in Love with a Lonely Girl” that seem bright and melancholy at the same time. He’s back on the Bar None label, which released his first albums, and he’s hitting the road for a brief series of shows beginning next week at City Winery in New York. “It’s not exactly a U2 tour,” he joked during an interview with Popdose in the late autumn, “but we’re going to hit a dozen or so cities with a band, and then I’ll fill it out with solo gigs. That’s the way I’ve had to do it for several years now, but I love doing the band shows whenever I can. Come to think of it, those band shows are coming up soon. I’d better get the group together quick.”

I was thinking about this interview last night while watching Heather Locklear on Melrose Place. I was thinking two things: one, it’s like 1994 all over again, and two, the health care bill must be in trouble.
(laughs) That’s funny! Yeah, my song was certainly part of 1994, and everything that went on then. But, hey, man, you’re lucky if you get to go through that once! It’s fun to reminisce about it, but life goes on. The beautiful thing for me is that people have a real need for music, and if you give them something good they will not say no.

You haven’t released a proper studio album since 2001. Why?
I don’t know why it took so long to make this record — why life does what it does. I know this: The response to the word that I actually have something coming out has reminded me why I do it in the first place. There are fans out there who say they’ve been dying for a new record, and that’s been nice to hear, because there have been a lot of times when I seriously doubted that was true. Maybe I have a self-esteem problem that I share with Katie Couric .

The fact, though, is that I made this record, let’s say, three times since 2001 – and even worse than that, I paid for it all myself. That’s the story behind it – me learning that I can’t make a record five times and expect to get by. Maybe I’m not the best businessman, but I decided each time to trash what I had done rather than put out something I didn’t like. It’s made me think of something my old friend [singer-songwriter] Kevin Salem said: “The done-ness of a song is the quality of the song.” I’m already dealing with this again, because now I’m trying to finish my next record, and I’ve got to get over the idea that the songs aren’t that good – it’s just that they’re not DONE. Everything has its time, you know? And those songs haven’t found their time yet. At least I have a title for the next record – it’ll be called Neon Repairman, which is a song that’s actually done.

You’ve moved around quite a bit in this decade, before ending up in Nashville. Is there any connection between that and the long space between records?
Yeah, there’s some connection, but all that was related to things I was going through that didn’t all have to do with the music. They were my problems—there’s nobody else to blame for them, no mysterious, evil backstory. I just didn’t make good decisions. I tried to self-produce a record, and finally I realized that it’s hard to make records! Other things in life tend to get in the way.

The new record has a big sound, which surprised me a little bit. This morning I was in the car and Steely Dan’s “Aja” came on the radio, and I connected the sound of that song to what you’re doing.
It’s kinda cool that you made that connection, because Aja was a pretty influential record for me. I love that album, even though I know most girlfriends hate it. The playing on it is so good — I’ve been hoping my whole career to get anywhere near that.

Much of what we’ve gotten from you during this decade has been covers – via the My Favorite Waste of Time album, as well as your gigs with the Know It All Boyfriends. In a couple places – maybe most obviously on “It’s Gonna Come Back To You” – it sounds like all those covers have had some impact on your own writing.
Absolutely, in a big way. I don’t know, maybe there’s something to be suspicious of, considering that since I joined the Know It All Boyfriends I haven’t managed to put a record out! Actually, being in that band helped me learn a great deal about songwriting — and it’s taught me a lot as a musician, as well. When you’re sitting around picking covers to play, there’s always some new chord to learn … but I had already gotten to the point where I was making things too complicated for myself, and in a lot of ways playing those covers made me see that keeping things simple is a pretty good way to go.

I didn’t expect it to have such a big effect on my writing. But you learn all these hooks from classic songs, and they get stuck in your head to the point where you realize you can mutate something enough to where you’re almost stealing it, but it’s original enough that you can get away with it.

I can think of a few people who’ve gotten very rich that way.
Yeah! You know, I get some criticism from fans that I play too many covers – they say, “Come on, Freedy, you’re such a dark songwriter, but all these covers you play are pop songs!” I’m sorry, man — I just like playing Paul McCartney and Matthew Sweet! I have to admit that I’ve been caving in to some bad consumer pressure, and now I’m trying to learn some heavier songs. But I’m not sure whether it’s going to work. I guess I don’t really know any Townes van Zandt numbers.

Apart from the songwriting influence and maybe the stunted career, what have you gotten out of the Know It All Boyfriends?
Oh, man, that’s the best thing I ever did as a musician … though not always. (laughs) For our early shows I would get super drunk and just mess around. I was a little bit embarrassed about it – we felt like the Replacements. But now we’re really good — we rock, in fact – and we’re getting better all the time. Of course, some of our friends are like, “I liked you better when you sucked.”

How did you re-connect with Bar None?
Well, they put out the record of my [early-career] demos [titled The Way I Were] in 2004, and I’ve always been buddies with them, we’ve always been in touch. It’s kind of just a full-circle thing. At first I didn’t even want to do that demos record – it felt like going backward – but they psychologically helped me through it. This business of “career retrospective” stuff — they helped me realize you have to just not take it that seriously. It’s all about the songs, you know? It’s the same with making new music – they helped me get past the concerns about just showing up again after having such a long time pass between records.

I realize I need to have a record out there to give people a reason to have me on their radio show, or at their club. I get so much advice from people who say, you need to reinvent yourself every time you make a record, you need to move forward and do something new and different every time. But it’s still really just about having a piece of plastic you can take to the radio station.

Well, when you go you’ll be preceded by publicity materials that say the new album sounds like “vintage Freedy” – which is a phrase that I have to admit I never imagined hearing.
“Vintage Freedy,” huh? Well, you know, I didn’t have anything to do with that. But it certainly is an unavoidable feeling, almost like having to prove yourself all over again. Man, eight years for many people is a whole career and a comeback! I never thought it would take eight years – but it doesn’t do any good to be anything but lighthearted about it. I don’t want to whine about it. You know, I got to put out a record every two years for about 10 years, and I’m glad I got to do that — that was my goal in life. I don’t know at this point if I could get back on that kind of schedule.

It’s a struggle, you know? Not just the writing and recording part, but the business thing, getting people in line to release your music and promote it and play it and host your gigs. Again, I’m not the best businessman. Some guys are good at it, some are terrible, but I’m really bad. It amazes me to see people who have the easiest time in the world succeeding in the music business. I’m always happy for them, because then there are people who are even worse than me, who can’t even get their pants on in the morning. I’m somewhere in the middle — I can get my pants on, at least once in a while.