It was just as expensive to live in New York City in 1969 as it is today and just as hard to find a place to sleep if you didn’t have enough loose change to grab a cheap hotel room somewhere. I had two couches in my apartment at 15 Charles Street. One was very large and comfortable; the other was small and suited for midgets or children. The large one was often occupied by assorted wandering jazz musicians and visual artists. Leo Meiersdorff was the first painter to crash and he stayed the longest, off and on over a period of almost three years. I had never been around anyone who turned out paintings on a regular basis and Leo was a painting machine in those years. I don’t remember how he turned up at my apartment, but I’m glad he did because he provided me with a wonderful array of record covers, posters, drawings and paintings for the next quarter of a century.

I’d come home from work and the living room would be littered with pictures, on tables, on the couch, on the floor. He was kind of hand to mouth in those days and every so often he’d gather up an armload of watercolors and sell them to a small gallery on 8th Street. It seemed as if he could sell his pictures about as fast as he could paint them, not for big prices, but big enough so he could eat regularly. He paid for the use of the couch with pictures and that was fine with me. I still have all the pictures and the couch is long gone.

Leo was German, six year older than I, something of a rascal, often unreliable and, in addition to being a great talent with a paintbrush, possessed a Kaiser Wilhelm-like moustache, of which he was very proud. I don’t think he was ever prouder than when he tired of being a bachelor and living on my couch, found a beautiful, but much younger woman to marry, and in the picture I took of Leo and Diana, his moustache appears to be almost six inches wide. 

Before he got married and moved off to New Orleans to set up shop in the French Quarter, he created the cover art for my first LP and three others in rapid succession, two of which are still in print forty years later. Over the years he created dozens of LP and CD covers, as well as posters for events I produced. Once he left town it was always a struggle to get him to finish anything and deliver it on time, but this was his only failing. With some people it’s about the check being in the mail when it isn’t but with Leo, he always had the check and I was waiting for the pictures. One time it got so complicated I took a flight to New Orleans to get covers for three LPs and while I was there managed to record Earl Hines as a bonus.

This is what happened. Earl Hines was scheduled to play a few weeks in a good room in New Orleans in November 1977. He had made my first record; I was coming up on my 100th release and I wanted it to be another record by Earl. He thought that was a good idea, I said I’d come to New Orleans to do it and I asked Leo to design the cover. Leo also owed me covers for Lee Konitz and Bobby Hackett LPs. If I was going to get them, I had to stand over him with a stick, or at least a big camera, which is exactly what I did.

The recording with Earl went very well, is also in print, thirty-five years later. The next day, I had a dinner date with Leo and Diana and their house. After we ate all we could Leo retired to his studio, got a pile of watercolor paper, and got to work. He turned out three beautiful covers that night. I had my 5”x7’ Deardorff camera with me and set it up outside his studio in the courtyard and took a picture of him working on the Earl Hines cover through the studio window. It is my favorite portrait of Leo. As I stood in the courtyard it made me think of the story someone told about the great Italian composer, Gioachino Rossini, who was late in delivering the manuscript for his new opera. This annoyed the impresario, who locked Rossini in a room until he completed the assignment. Just like Leo, Rossini worked quickly under pressure, kept composing and throwing the manuscript out the window, page by page, until it was complete. Leo didn’t throw the paintings out the window, but he did finish three oversized watercolors for album covers in a couple of hours.

I’ve often wondered what would have happened if Leo hadn’t been so prolific with his jazz and cooking pictures. He once created a series of very large paintings which were decidedly non-musical, two of which hung in my Christopher Street studio for years and are now, unhappily, in storage, simply because they are too big. They are much like Helen Frankenthaler and quite wonderful. But the light work of musicians and chefs was easy, commercial and in demand. 

Leo and Diana separated and he drifted away to the West Coast, first to Washington and then to southern California, where he remarried, this time to a grown-up, Jennifer Leonard. He continued to paint and I continued to ask him to design all manner of things. The last was a CD booklet cover for a Jay McShann release entitled Some Blues. It was one of his best designs for a jazz recording. I had asked him for another in the same vein but it never arrived.

He was never in good health all the years I knew him, primarily suffering from diabetes, which he tried to control with diet instead of insulin. This finally caught up with him and in the mid-1990s various health issues came to a head, he was hospitalized and somehow managed to contract a virus in the hospital that attacked his heart and killed him very quickly. Jennifer told me that the sketches for my CD were on his worktable. 

It’s now fifteen years since his premature death and his vibrant pictures are all over hundreds of web sites, as well as the walls of my office. On the Internet you can find hundreds of examples, all the way from cheap reproductions by people who have stolen his designs, to original watercolors that sell for many thousands of dollars. All of his paintings are terrific, but the ones he created of jazz musicians were special and they were never better than when they were just lying on the floor of my living room, waiting to be scooped up and delivered to that dealer on 8th Street who had no idea of what treasures he was getting for pocket change.

Leo Meiersdorff, In His Studio, New Orleans, November 1977