The pairing of Thelonious Monk with Gerry on a recording seems to many an unusual idea. Gerry speaks of his friendship with Monk and how an impromptu session in the recording studio with this artist happened.
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Well, the one recording with Thelonious [Monk] came about by accident because he and I were pals and we visited back and forth. We only lived a few blocks away from each other and spent a lot of time together. So I'd be over at his place a lot, but oddly enough we never played together. We were always hanging out at his house talking about writing, and we would show each other things we were doing on piano and ideas that we had for orchestration and so on. And I spent a lot of time transcribing some of his tunes that he didn't have written down.
Good Neighbor Thelonious / Thelonious Monk. Performed by Gerry Mulligan. From the Album "Lonesome Boulevard." 
So, he had a recording date with Riverside, and I found out about this from Orrin Keepnews, who said that Thelonious went down to the office one time to talk about this date and it came up in conversation that Gerry Mulligan was waiting outside for him. Keep said, "Oh, you know Gerry?" And Thelonious said, "Yeah, we're old friends."
As it turned out, they had wanted originally to do the quartet that Thelonious and John Coltrane were playing with down at the Half Note. But Coltrane was tied up in a contract with somebody else and they couldn't get a release for him to play with Monk on the Riverside album, and so they were kind of stuck. I guess they were thinking that Thelonious would make a trio album, but then when Keepnews found out that Thelonious and I were friends, he asked if Thelonious thought I would record something with him. Monk said sure, and so that's how that came about. I said I'd do it and I felt like I was walking on a tightrope because, not having every played together, I was feeling my way. The way that Monk accompanies you, and the way he approaches chord progressions really demanded a whole different melodic approach from me. I could hear in places where I was getting it together, like getting into a groove with him that really fit, and in other places that I was really kind of stumbling because I couldn't find my way. I kind of marvel at my guts to go record something like that, to put myself in the frying pan that way. But that turned out to be the only time we ever recorded anything together, which in itself was kind of a happy accident. I'm glad we did it, even if it's got big bruises on it.
- Riverside, founded in New York by Bill Grauer and Orrin Keepnews, began in 1953 by reissuing historic recordings the famous "Jelly Roll" Morton recordings and interviews made for the Library of Congress by Alan Lomax were among them but inaugurated a modern jazz series in 1954 with major new records by Monk, Montgomery and Bill Evans, among others. (back to transcript)
- The Half Note was at Hudson and Spring Streets in Greenwich Village from 1957 to 1972. Al Cohn, John Coltrane, Charles Mingus, Zoot Sims, and Lennie Tristano were among the major artists who played there. (back to transcript)