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Now the process is low-fi, informal, fast.
He has no plans to release an album and he still doesn't sell CDs. But a couple of years ago, he made an exception and agreed to sell at least 150 copies of a compilation called November Nights.
The fact that the CD exists speaks to Iceberg's role as a life force in Kansas City music.
Abigail Henderson of the Gaslights remembers Iceberg from his Wednesday-night gigs at the Grand Emporium, nearly a decade ago. "He was this amazing songwriter with this crazy voice and this amazing way with words, and I was completely enamored with him," she says. Henderson wasn't in a band; she was mostly messing around with a guitar in her apartment by herself. "One night, I asked him, 'I wrote these songs — would you listen to them?' I played him a cassette in my car. He said they were good, and I was like, 'Oh, wow, Howard said they were good!'"
One of the songs she taught herself to play guitar with was Iceberg's "Play Me a Slow One," a breakup lament from the perspective of a torn-up man in a barroom.
"I told him how much I loved it because it's beautiful — tragic but beautiful." Later, when Iceberg saw her at shows, he invited her onstage to play it with him. One night at Davey's, opening for John Doe, Iceberg saw Henderson in the crowd and invited her up. Henderson's fierce harmonies changed "Play Me a Slow One" from a breakup song into an argument for reconciliation and connection.
Someone happened to be videotaping the set.
In July 2008, Henderson got the grim diagnosis of rare and aggressive inflammatory breast cancer. Area musicians rallied, putting on an event called Apocalypse Meow. It has become an annual benefit and has given birth to the nonprofit Midwest Music Foundation.
Tony Ladesich drove much of the planning for that first event. "Knowing that Howard doesn't sell CDs, I asked him to put together a few numbered editions of the complete Howard Iceberg recordings, and we'd sell them for a couple hundred dollars apiece," Ladesich recalls. "I said, 'Howard, you have to get all the recordings together and put them all out there.' He said, 'OK, maybe that's a good idea — for Abigail.'"
After kicking the idea around, Ladesich says, Iceberg suggested that instead of putting out a limited boxed set of a couple of hundred songs, they would put out a 13-song CD. They also created a special DVD edition with the video from that night at Davey's.
Iceberg still gets requests for duplicates of November Nights, which he burns one at a time and gives away. "I didn't want to charge once the commercially produced CDs were gone."
Now, nearly two years after her diagnosis, Henderson is free of cancer.
That live version of "Play Me a Slow One" is her only performance with Iceberg. But it's just as much a part of Iceberg's nonstop recording project as the songs produced in Tomek's studio.
"I remember learning how to play it and then singing it and being so excited that I could sing with Howard," Henderson says. "It's weird that things came full circle."
That observation wouldn't surprise Ladesich.
"Howard is part shaman, part guru," Ladesich says. "He's a not-spiritual spiritual adviser to the songwriting community. He understands something on a deeper level than most people."
Ladesich says he considers himself a student. "I will soak up any knowledge he cares to offer. The problem is, he will never offer any knowledge to you if you go to him as a student. Howard wants to meet you on a level playing field because he truly believes he has just as much to learn from anyone as he has to teach."