“DORSEY WAS THE greatest melodic trombonist in the business, but he was a drag to work for,” Buddy Rich said, understating the case. TD’s theme song was “I’m Getting Sentimental over You.” And there is a quality to his playing, perhaps especially when he mutes his horn, which for want of a better word one might call sentimental, sweet, or soulful. But he was anything but sentimental in matters of money. When Sinatra decided to go out on his own, Dorsey forced him to sign a punitive contract that would grant Dorsey a percentage of all the singer’s future royalties. Sinatra thought it worth the risk. Later he managed to slip out of the contract altogether, though it cost him plenty. “I hope you fall on your ass,” Dorsey told the singer. Dorsey wanted Sinatra to fail, and Sinatra never fully forgave him, though he did turn up unannounced to toast the bandleader and sing at a memorable Dorsey tribute in New York in February 1955. (If you can find the CD called This One’s for Tommy, featuring Sinatra and Jo Stafford, buy it.) One of the first albums Sinatra did with the Reprise label was I Remember Tommy in 1961, with arrangements by Sy Oliver. A treat: play the 1961 versions of “East of the Sun (and West of the Moon)” and “The One I Love Belongs to Somebody Else” back to back with recordings the old Dorsey band made twenty years earlier.
Years later—in Los Angeles, in June 1979—Sinatra introduced Harry James to a live audience. James was a great guy. James had let him out of his contract after only six months. “And then there was Tommy Dorsey,” Sinatra said. “And when I wanted to get out of my contract to him years later, it cost me seven million dollars.” Suddenly the specter of Tommy Dorsey materialized before him as a ghost before a Shakespearean prince. “You hear me, Tommy? You hear me? I’m talking to you.”