About a week ago Nicholas Tremulis expanded the family business. He was working on three new songs at Rax Trax Recording, a Lakeview studio owned by his longtime bandmate Rick Barnes, and he decided to have his nine-year-old daughter, Electra, sing backup on one of them, an R & B-meets-mariachi reworking of Edgar Eden’s gospel tune “Satan’s Jewel Crown.” “It’s her first microphone appearance,” says Tremulis. “There’s something cute and weird about hearing her little voice sing, ‘Satan’s jewel crown / I’ve worn it so long.'”

Tremulis will release the track this week as the latest installment of 52 Reasons, an online song-of-the-week project he began in February. “I was tired of labels and waiting around for them to put records out on their schedule,” he says. “This allows me to write something, record it, get it out, and get an immediate reaction.” So far he’s released 23 songs through the Brooklyn-based online music company Reel to Reel Records (reeltoreelrecords.com), which says he’s consistently selling 500 downloads a week.

Shortly after 52 Reasons debuted, Tremulis helped start The Eclectic Company, a two-hour program on WXRT he hosts every other Monday, alternating with Jon Langford. Tremulis had talked with the station about doing a “free-form music thing” since the late 90s, and the show gives him an opportunity to spin Gypsy jazz, punk, and blues all in one sitting. He’s also invited guests like David Johansen, Robbie Fulks, and (full disclosure) myself to play their own favorites.

Tremulis’s career has been defined by that sort of far-flung eclecticism, though it’s proved to be as much a curse as a blessing. A lifelong Chicagoan, the 45-year-old was born in Greektown and raised in Northbrook. He grew up in a musical family: his father played jazz piano, his mother moonlighted as a blues singer, and a cousin played guitar with Curtis Mayfield. By the time he hit his teens Tremulis was an ambitious guitarist, making regular trips to blues clubs in the city, sitting in with the likes of Mighty Joe Young and Lefty Dizz. Inspired by Ornette Coleman’s 1973 album Dancing in Your Head, in the early 80s he formed the Nicholas Tremulis Band, which he describes as a “cross between punk, the AACM, and James Brown.” The group quickly expanded into a 13-piece soul band and became a popular local headliner, also opening for big-name touring acts, including Tina Turner, Sheila E., and Grandmaster Flash.

Tremulis’s vocal style at the time was heavily influenced by R & B, a trait that confounded some of the labels that approached him. “I lost two record deals when they found out I was white,” he says. “Tommy Boy asked me if I could darken my pictures a little–I thought that was funny.” Tremulis eventually signed with Island Records, which released his 1985 self-titled debut and 1989’s More Than the Truth, but both albums were crippled by the effects-heavy, inorganic aesthetic of their time. Sales were weak, and Tremulis disowns the records now. “If I could buy every copy and start a big fire, I would,” he says. “They’ve haunted me ever since.”

When Island head Chris Blackwell sold the label to Polygram in 1989, Tremulis opted out of his contract and decamped to New Orleans. There he played and recorded with Ivan Neville and Meters bassist George Porter Jr. and rethought his career. “Maybe it was being in a city that had learned to borrow from a bunch of musical styles in a really pure way, but I just started getting back to the roots of things that I really liked,” he says.

Upon his return to Chicago he assembled the six-piece Nicholas Tremulis Orchestra and recorded a pair of darkly atmospheric independent albums, King of the Hill (1994) and Bloody Show (1996), both of which featured contributions from beat poet Gregory Corso. But his lackluster performance on a major label seemed to have damaged his rep, and Tremulis admits his mood darkened in the mid-90s. “At the time that the alternative craze kicked in and bands started getting signed out of Chicago, there was a period of time here where if you were an older artist like myself you were pretty much shit outta luck,” he says. “It felt bad and disrespectful in a way. At that point I had to start asking myself, ‘Why are you still doing this?’ I realized I do this because I love it. And that’s when I really became a musician. I pretty much got into music and out of the business all at the same time–it was really like an epiphany.”

Inspired by the Band’s farewell “Last Waltz” performance, in 1999 he staged the first of his Waltz concerts, all-star benefits for the local charity for the homeless Neon Street that featured big guns like Billy Corgan, Steve Earle, Mavis Staples, and the Band’s Rick Danko, who contributed to Tremulis’s rootsy 2000 album, In Search of Woodfoot, shortly before he died. But after the fifth Waltz, in 2003, Tremulis put the event on indefinite hiatus. “It just got tougher and tougher to do each year logistically,” he says.

In Search of Woodfoot came out on QRS Records, a label Tremulis cofounded with producer Rob Fraboni, but without a distributor the album received little attention. Last year the Texas Music Group released Tremulis’s follow-up, Napoleon, which featured a mix of moody pop, cocktail jazz, and smoky R & B, but he wasn’t able to tour much in support of it. “It’s tough to really get a six-piece band on the road and make money,” he says. “Plus all the guys have lives and families here.” (Tremulis and his wife, Penthea, have two children.)

To keep afloat in the years between releases, Tremulis does session and commercial work; he’s recorded with Corgan and Keith Richards and played on jingles for Bud Light and Nintendo. But his work on 52 Reasons, a winning assortment of tunes mixing bossa nova, reggae, Delta blues, and more, has him feeling optimistic and ambitious. Tremulis hopes to have enough material for four CDs by February: two discs of originals, one of covers, and one of spoken-word pieces. (“Satan’s Jewel Crown” kicks off a subset of 52 Reasons featuring reimagined 20s gospel tunes.) And though his cynicism about the record industry was a key inspiration for the project, he believes it might eventually attract a label. “People are willing to take a chance and check out a song,” he says. “It’s already exposed me to people that never would’ve had a chance to hear my music.”

In the meantime, Tremulis is preparing for a rare road trip. This week he and his band will head to Texas, headlining two shows, backing former Beach Boy and Rolling Stones sideman Blondie Chaplin at another, and making guest appearances with Alejandro Escovedo and Hubert Sumlin at two more. But the band can only afford the excursion because a wealthy fan has hired the group to perform at a private party in Paris, Texas.

“To be honest, at this point I would just as soon have some rich guy pay for my musical career, because I’m really tired of jumping around to different labels,” he says, laughing. “I wouldn’t mind being a kept boy. But that ain’t gonna happen, so I’ll keep bouncing around. Whatever it takes, I’ll keep bouncing around.”

Art accompanying story in printed newspaper (not available in this archive): photo/Joeff Davis.