The term 'Sing Like Sinatra' can be summarized by the crossword solution 'CROON, ' which is a five-letter word. Crooning is a type of singing that is characterized by a soft, gentle, and smooth vocal style. It was popularized by singers such as Frank Sinatra, Bing Crosby, and Nat King Cole in the mid-20th century. Singing like Sinatra, then, would involve crooning in the same style as these iconic singers.