Songwriters Mike Benign and Allen Keller can still remember one another from their days working in and around Milwaukee during the ’90s. Back then, both fronted bands – Blue In The Face and Arms & Legs & Feet for Benign, Falling Wallendas and Women’s Liberace for Keller – and each agrees the other’s work was miles ahead of his own.

"My sense of him was that he was in a much different league than me as a writer – meaning a much higher league," Benign laughingly said of Keller, to which Keller was quick to counter with, "Arms & Legs & Feet were really an important band … I felt that was in a different league than I was. It really inspired me to take my next band to another level."

Despite their artistic appreciation for one another and relative proximity, however, the two never really collaborated back in those days. Instead, they continued on their separate paths; Benign’s track kept him playing in Milwaukee with those two ‘90s projects and then eventually his current band, The Mike Benign Compulsion, while Keller’s took him out of the Cream City – and eventually out of music altogether.

Several years later, however, the fates finally brought the two together for a new joint-project called "Happiless," the duo’s ten-song self-titled debut just released Aug. 1 on iTunes, Amazon, Bandcamp and CDbaby. And while the connection between the two Milwaukee-bred songwriters would seem to be obvious, the path to getting to this point was less than simple.

The idea for "Happiless" originally came to Benign courtesy of another musical pairing: Aimee Mann and Ted Leo’s 2014 release "The Both" (which conveniently enough features a song titled "Milwaukee").

"I had been big fans of both of them, so I knew how strong they were individually as writers and as singers and performers," Benign said.

"What was interesting to me is that they were both alphas; they were both people who were in charge of their own musical careers and were principle writers. So aside from everything I like about the two of them musically, it was also intriguing to me that they were two people who were solo artists and solo writers for much of their careers, and figured out how to work together. It seemed to me like a pretty good blueprint for how that might work – especially since it’s something I’ve not really done."

With that blueprint laid out before him, Benign took his "excess of material or ambition or free time" on his hands and began formulating songs for the album – as well as a pitch to the one person he thought could help bring his dream duo to life: Allen Keller. 

"I always had this idea that I would love to write songs and have a singer that I really liked sing them," Benign said, "and I was always a fan of Allen – both as a writer and as a singer – in the bands that he was in around Milwaukee and Chicago back in the day. So I reached out to Allen to see if he would be interested."

The only major roadbump in Benign’s plan: Keller was no longer really in music. In fact, he hadn’t written a song this side of Y2K.

"I had completely given up songwriting and I actually had pretty much a total life change since I was doing music," Keller said. "I’d been picking up this guitar for the last couple of years, and I’d just really completely forgotten how to write. I couldn’t come up with two or three chords that I thought were good enough. I stepped away for a long time, and I think I kind of expected to go back to the proficiency I once had, and when I realized that it was going to take more work, I kind of lost faith that I could ever write at the level that I expected of myself."

Part of the problem, Keller noted, was that his life had changed so drastically since he had last written music.

"I’d moved – I went from Chicago to Los Angeles – I had a family, I was a comedy writer; I’d completely changed everything about my life," he explained. "I kind of wrote misanthropic stuff before, and I didn’t really feel that way anymore, so it was hard finding not just the chords to play but the frame of mind or perspective to write from.

"I find that a lot of artists don’t transition well; the angry young man guy doesn’t really turn into the stable older man and write interesting songs – or at least I think."

With enough pestering and cajoling, however, Benign managed to convince Keller to help him write some new music – or at least consider helping him. While Keller was still on the fence, Benign would send him pieces of songs for "Happiless" that he was working on, simply requesting perhaps a stanza or just even moving the song forward, to take it to the next level. But Keller still struggled with rediscovering his songwriting voice.

"I just couldn’t do it," Keller said, "but the material he was sending me was so good that I wanted to be a part of it. So I just kept trying until finally I found my writing style again."

Keller credits the track "Pill Called The Disaster" for helping first crack through his long-frozen chunk of writers block.

"My training wheels were working on Mike’s stuff that he started, but anytime I tried to start my own song, I hated it; I wouldn’t even show him anything," Keller recalled. "And then ‘Pill Called The Disaster’ kind of hearkened back to my material with the Falling Wallendas, and I think that kind of was a breakthrough for me. It made me feel like I was back to where I’d been."

The duo continued on from there, following the blueprint of Mann and Leo before them by emailing tracks, chords, additions and other pieces to the "Happiless" puzzle across the country (while Benign still lives in Milwaukee, Keller now calls Los Angeles home).

By the time the tracks were figured out and mapped out, Keller and Benign reached about a "50/50" split on the workload, with their different approaches toward creating music complementing one another even more than they could’ve imagined at the start.

"As we got on, Mike would have a million ideas, but I was the one who’d take one idea and just work it to death, and I would not let go," Keller said. "I would just keep doggedly working on this until I thought it was done – and by that time, Mike’s got another 10 songs in the works."

Benign added, "For me, the thing was writing with somebody else and having to meet in the middle or just say, ‘No, you’re right; that idea’s better.’ So that was a learning thing for me; I’m not used to that. And stylistically, Allen’s right: We are a lot different. I tend to be less meticulous about every detail than Allen is. But I think that’s great. Allen has a knack for arrangement that I don’t have and for ‘how do we make this not exactly what you’d expect?’

"That’s where I think the collaboration comes in, where we’re each bringing stuff to the table and we’re coming at it from a different perspective that the other doesn’t have, which may sound like a cliché, but that is the reality."

The duo eventually brought the 10 new songs out to Keller’s current home base of Los Angeles. There, Keller’s extra contribution as, in Benign’s words, "the rich kid in the neighborhood who had all the cool toys," came to the forefront, bringing in several of his music industry friends – including colleagues who’d worked with the likes of Melissa Etheridge, Fountains of Wayne, Dwight Yoakam and more – to help with the recording process.

The result is a 10-song demonstration of cross-country, cross-technology teamwork. And what’s next? What’s the future hold for the duo? Neither is quite sure yet; after all, they each have their own individual projects to focus on as well. Benign still has his band here in Milwaukee, while Keller is a screenwriter with a film currently in the works. But that doesn’t mean they’re not tossing some ideas around – however serious they may be.

"I think the next thing I’m going to do is I’m going to pitch Allen hard on co-writing ‘Bat Out of Hell III’ for Meat Loaf," Benign joked. "Or maybe ‘Bat Out of Hell IV’; I’m not even sure which one they’re on now."

"We should probably do ‘Bat Out of Hell V’ just to be sure," laughingly added Keller.