I met Bob Cranshaw when I was doing the first Playboy Jazz Festival in Chicago in 1959. Something happened to my bass player and the people in Chicago said, “Try Bob Cranshaw.” Bob came by and I heard him play. I played some of the stuff that was in my set then, and I made some modulations, and he was right there with me. He was nimble enough to follow the things that I was doing, which was what I was looking for. I also like to play calypso music, because I have Caribbean heritage, and Bob could play calypso. At that time you did not run into a lot of jazz musicians who could play calypso, but people had gotten used to hearing me play calypso at my concerts. So Bob filled that capacity as well, and it endeared him to me musically. That was an important reason why I always sought him out. He fit the bill.
That was before the time when I went to The Bridge. I told Bob that I was going to be taking a hiatus for a while, but that when I formed my band when I came back I would invite him to play with me. So he started really working with me during the 1960s, after The Bridge.