Miki Greenberg’s new double CD, Retrospectacle, could be described as a greatest-hits collection–if Greenberg had ever had a hit. As it stands, all but 2 of the 15 records he’s released since 1987 are out of print, including one that came out in December. That the other two are “in print” simply means that Greenberg has some copies available for any takers. “I just sell a few hundred records to people who find out about me, and I use it to break even on these really cool projects,” he says. “It’s very artistically pure.”

Greenberg’s music, though quirky, isn’t willfully obscure. He describes it, accurately, as “pop and catchy, but a bit odd,” and he repeatedly mentions Cole Porter and the Beatles as models of songcraft. And as a veteran of the avant-cabaret band Maestro Subgum & the Whole, which had a strong local following in the late 80s and early 90s, Greenberg has his fans–like Colleen Miller, who books the Old Town School of Folk Music, where Greenberg runs the cafe.

“I’d heard about Maestro when I was in college,” Miller says as Greenberg serves her lunch. “And I never went.” Still, in 2001 she orchestrated a sold-out Maestro reunion show at the Old Town School. Later that year Greenberg put out a record with a new band, the Fetal Position, and cemented Miller’s loyalty. “The Fetal Position record, that was awesome,” she says. “That definitely would be when I became a superfan.”

Greenberg started writing songs in 1979, when he was 17 and living in Boston. “I didn’t play an instrument and at first I wasn’t even sure I was writing songs,” he writes in the liner notes to Retrospectacle. “Something would be stuck in my head and I would try to remember which band did the song. Then I would realize that I had made it up.”

He moved to Chicago six years later, figuring to make his way as a photographer, and promptly fell in love with Kate O’Reilly, whose brother Beau led Maestro. Before long Greenberg was writing songs and playing piano with the band. In 1994 he sold his photo equipment and his Bucktown home and studio, and sank the proceeds into the Lincoln Avenue building that became the Lunar Cabaret, home to Maestro and its theatrical offshoot, the Curious Theatre Branch. Asked if the enterprise, which included a modest restaurant, the Full Moon Cafe, provided enough money to live on, Greenberg laughs. “Well, it was enough to die on,” he says. “I went into Lunar with an incredible credit rating and tons of money–and came out three years later bankrupt.”

The Lunar carried on a storefront theater, with Greenberg as its landlord, until early 2003. From 1997 to ’99, when he took the job at the Old Town School, Greenberg made a living answering the phones and filling tape orders at This American Life. Maestro had petered out, but Greenberg put together an art-punk band called World Gone Mad (which later morphed into the Fetal Position), and in 2002 he took a year off from performing and recording to write and regroup. In March 2003 he released Miki Greenberg’s Songs of Tenderness and Love, which he celebrated with another Old Town School concert. All 250 copies of All I Want Is Sex for Christmas, which came out in December, went to friends.

The idea for Retrospectacle came to him as he prepared to start work on the next Fetal Position project, The Oral History of Anal Sex, which comes out this month. “It just seemed to add up,” he says, to put out a compilation “before this thing gets so big that I can’t even get my arms around it.” The resulting 38-song collection includes lush orchestral pop, cabaret numbers that seem influenced by Kurt Weill and Stephen Sondheim, loud funk-inflected rock, reflective ballads, solo piano pieces, and goofs like the title song from Sex for Christmas.

A June 12 release party for both new CDs will feature the eight-piece Fetal Position band, includ-ing trumpet, clarinet, and cello, as well as guest ap-pearances by Jenny Magnus, Beau and Kate O’Reilly, and Old Town School teacher Shana Harvey. Greenberg and O’Reilly’s 12-year-old daughter, Max, will sing two numbers, including “Runaway,” an antiparent punk-rock screed that she recorded with Greenberg when she was seven. Sharing the bill are Greenberg’s coworkers Kennedy Greenrod, who performs as the Thin Man and who’s celebrating the release of his band’s CD H.M.S. Mandegreen, and Liam Kimball, best known as the singer and bassist for New Black.

“We’re a community of musicians,” Greenberg says of the cafe’s staff, “and this is one of the ways you celebrate community. Everything I’ve done, I’ve always run it as a community. When I serve people here, I’m serving them like my family,” he says, handing a colleague some pasta salad. “It’s love that I’m serving.”

The Fetal Position, the Thin Man, and Liam Kimball perform Saturday, June 12, at 8 PM at the Old Town School of Folk Music, 4544 N. Lincoln. Tickets are $12, $10 for kids and seniors. Call 773-728-6000.

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