Betcha’ didn’t know that. I didn’t either, until I read James Kaplan’s biography, “Frank: The Voice” (Anchor Books 2010). As a teenager, Ol’ Blue Eyes was entralled by the singing of a newly emerging crooner, Bing Crosby. After seeing Crosby in the film “Waikiki Wedding,” Sinatra took to wearing a yachting cap just like Crosby’s, smoking a pipe, and strumming a ukulele his uncle had given him.
Too bad Sinatra didn’t stick with the uke. One can only imagine how hip his version of “Tiptoe Through the Tulips” would have been. (As it turned out, it’s one of the very few great songs Sinatra never recorded.)
The book is great, by the way. It ends in the 1950s with Sinatra winning the Academy Award for his acting in “From Here to Eternity,” so one hopes that the author has Vol. II (and maybe even Vols. III and IV) in the works.