Remembering Larry Penn

Larry Penn

Larry Penn

Larry Penn, who wrote wonderful songs such as “I’m a Little Cookie,” passed away on October 7 at his home in Milwaukee. He was 87 and died from complications of diabetes and heart problems.

Larry will be fondly remembered as a folksinger, songwriter, truck driver, Teamster, member of the Rose Tattoo, toy maker and wonderful family man who will be deeply missed by his wife of 62 years, 4 children, 8 grandchildren and one great-grandson. He will also be mourned by his numerous fans and folks who discovered his songs through songbooks, community sings and concerts.

I first met Larry back in the early 1980s at one of the early Great Hudson River Revivals, sponsored by the Clearwater. This was pre-CD days, and I remember Larry lugging around a box of LPs of his then-new recording I’m a Little Cookie. He gave me a copy, and it has been a cherished part of the WFDU-FM collection ever since.

Being a fan of railroads and some-time model railroader, I immediately put the needle down on a track from the LP called “John Allen’s Railroad,” a song about a legendary model-railroader who turned his miniature trains into an art form, creating life-like scenery and true to life operations on an enormous model railroad built in his home. The storied model railroad, which he called the Gorre & Daphetid, became a legend among model railroaders and was featured in books and magazine articles about the subject. The model railroad was consumed by a fire 10 days after John Allen passed away in 1973. Larry Penn, an avid railroad enthusiast, captured the spirit and passion of Allen’s hobby in his beautiful song tribute.

Other songs on that album soon became favorites on my playlists. The song “I’m A Little Cookie” was inspired by his wife, who worked in at a children’s center in Milwaukee and wondered why there were no songs about emotionally disturbed children, often sadly referred to as “damaged.” Larry recalled a local bakery where he bought bags of broken cookies at a discount, which he fed his own children because although they were broken, they tasted just a good as any other cookie. Larry’s song has since been recorded by over 30 artists, including John McCutcheon and the late Pete Seeger.

Larry’s songs were true folk songs- they were about the joys, struggles and history of the people he sang to. You won’t find any real personal songs about Larry in his canon, he did not write about himself, choosing to focus on the stories of the people and issues in the world around him. He drew inspiration from his children, and Larry would perform for audiences both young and old.

Larry picked up the guitar during the later days of the folk revival, inspired by music he had heard from LP’s by folks like Lead Belly. Eventually he found himself on stages, and he would often work a full shift driving a truck and then perform in the evening.

In 1976, Joe Glazer invited Larry to sing at the George Meaney Center for Labor Studies in Silver Spring, Maryland and also recorded Larry’s first album called Working for a Living, released on Glazer’s own label, Collector Records.

After retiring as a trucker when he was 58, Larry became a full time musician, writing songs and performing at festivals, schools, museums and the annual Hobo Convention in Bitt, Iowa. He became a member of the Rose Tattoo, a loosely organized fraternity of traveling musicians who honored the legacy of the hoboes and tramps they often sang about in their songs. The spiritual leader of the group was Bruce “Utah” Phillips, and you can say that Utah and Larry were cut from the same cloth.

I will be paying tribute to Larry during the 3pm ET hour this coming Sunday, October 19. (You can listen in through our website at or through iHeartRadio .) I will feature excerpts from an interview I conducted with Larry at the 2002 Old Songs festival, where he was performing with the Rose Tattoo. I will feature a number of Larry’s songs.

A public celebration of the life and music of Larry Penn will be taking place on the same day from 5:30 to 8:30pm at the Anodyne Coffee Roastery, located at 224 W. Bruce Street in Milwaukee, Wisconsin.

About Ron Olesko

For over 40 years, Ron has been a radio programmer with WFDU-FM in Teaneck, New Jersey. He created WFDU-FM's TRADITIONS in 1980, a show that he continues to host and produce every Sunday afternoon from 3 to 6pm Eastern Time. He's the president of and booker for the Hurdy Gurdy Folk Music Club in Fair Lawn, New Jersey, and is a regular contributor to Sing Out! as well as the host of the Folk Music Notebook blog on this site. Ron can also be found emceeing concerts and festivals around the NYC/NJ area. A lifelong Mets fan and a rabid soccer geek, Ron is a Red Bull season ticket holder since their inception and will most likely be in his seat when not in the studio.


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