There's a very nice obituary for Larry Penn in the Milwaukee Journal Sentinel:

Larry Penn remembered for his musical prowess, and compassion

By Jan Uebelherr of the Journal Sentinel Oct. 9, 2014

Larry Penn was once a Teamster, a ponytailed truck driver for the Ladish Co. whose love of folk music grew from playing the air guitar to a real one — at the suggestion of his wife — and writing songs. Truckloads of them.

Penn, best known for a song called "I'm a Little Cookie" — recorded by the late legendary folk singer Pete Seeger and local folk singer Claudia Schmidt, among others, died Tuesday at his Milwaukee home of complications of diabetes and heart problems. He was 87.

"He represented a lot of history that we as a people share — labor history," said his good friend, Chicago-area folk singer and songwriter Mark Dvorak, who met Penn in the late 1980s and performed and recorded with him.

"When I first me Larry, he took me around to all the spots where things had happened — the Bay View massacre, scenes of strikes. People don't always like to hear about it, but that is a part of our shared history and he wasn't afraid to bring to the stage," Dvorak said.

In the folk music heyday — especially the 1970s — Penn would work an eight- or nine-hour day driving a truck, then perform.

He caught the attention of Joe Glazer, a performer and owner of Collector Records, in 1976 — the bicentennial year — when labor was also "searching for its roots," Penn later recalled. Glazer invited him to sing at what was then the George Meany Center for Labor Studies in Silver Spring, Md. Glazer also issued Penn's first album, "Working for a Living," a collection of labor songs. And things began to take off for Penn.

At 58, Penn retired and turned his full attention to his music. Over the years, he often performed and recorded with Lil Rev and others, including singer/songwriter John Sieger of Semi-Twang.

"It was unfair to be on stage with Larry," said Sieger, who played several times with Penn at Cafe Carpe in Fort Atkinson. "The guy who followed him would always lose. Larry didn't have any clunkers."

Penn represented a vanishing breed of folk singer and songwriter, he added.

"He didn't write about himself. That's what folk music is now — it's a mood ring," Sieger said. "He wrote about trains and trucks and union men and people shooting each other and people who were different."

He pointed to an anti-gun song called "The Shovel is Brother to the Gun," the title borrowed from a Carl Sandburg poem. "It's both funny and deep," Sieger said.

In a 1988 interview with the Milwaukee Sentinel, Penn had conceded that he was not your typical truck driver. He had a pony tail and beard before truck drivers did that kind of thing.

"I was never the darling of the truck driving set, that's for sure," he said.

But with an undisputed blue-collar pedigree as a "working stiff," he became the darling of those who appreciated great folk music.

"Train songs — it's almost impossible to write a bad one," he said in the 1988 interview. "You can't hardly write a train song people don't like, at least to listen to." The 1988 feature story called "End of Train Device" one his finest train tunes, "a lament for the gradual replacement of the caboose with a computer sensor."

And then there was the cookie song. It was inspired in part by a long-ago Milwaukee cookie factory, and in part by a song he and his wife, Pat, heard at a music festival. The song was about being an "illegitimate child." His wife, who worked at Penfield Children's Center, wondered why there couldn't be a song about emotionally disturbed and "damaged" children.

Penn told the tale of the cookie factory in the liner notes of his 1983 album, also called "I'm a Little Cookie":

"We had a cookie factory here in Milwaukee that used to hang up a shingle every week or so. It read, 'Broken cookies!' Then the people ... could go and buy pounds of broken cookies for $1.25. You could take those home and just pig out, but after you got into 'em you realized that they tasted just as good as the cookies you bought in the store and got maybe eight in a package for 89 cents."

Penn explained, "Once the two ideas met, the song took about three minutes."

He recalled that Pete Seeger told him, "Any fool cold have written this, but no fool did."

He added, "Actually, there's no big brainstorm about the song."

"He was very much a poet," Dvorak said, and a focused, natural songwriter. "He was a hard thinker. I'm not sure he knew how he did it...I think he just found that place."

It helped that he was focused on a cause. Dvorak remembered being on a boat fishing with Penn. "He gave me a lecture. And I couldn't get away from this one. Couldn't change the subject either," he said. "He told me about the role of labor and his opinions about it. What I learned is, you can't turn your back on this stuff as an artist, if you know about it and care about it.

"And he cared about it because it matters. We hear the word 'passion' a lot these days. We don't hear the word 'compassion' a lot. He had compassion for working people."

Penn is survived by his wife, Pat; daughters Genevieve Penn, Nancy Penn, Terry Penn and Sharon Monahan; seven grandchildren and one great-grandson.

A private memorial service is planned. A public musical celebration of life will be 5:30 to 8:30 p.m. Oct. 19 at Anodyne Coffee Roastery, 224 W. Bruce St., Milwaukee