This is a brilliant version of the song, beautifully sung by Sinatra, but it’s not entirely convincing emotionally.  It’s from the 1956 Capitol album Where Are You? on which Sinatra worked for the first time with arranger Gordon Jenkins.  (He’d done most of his previous work at Capitol with Nelson Riddle.)

Jenkins went for a lush, smooth sound, less jazzy than Riddle’s arrangements.  Sinatra generally used Jenkins for sentimental ballads, closer to the feel of those he did with Axel Stordahl at Columbia earlier in his career.  He follows Jenkins’s lead here, delivering a lush, smooth vocal that favors the musical over the dramatic.

Dylan covers it on his album Shadows In the Night and brings the dramatic, melancholy side of the song closer to home.  It feels very personal.  When Dylan sings the opening line — “The falling leaves drift by the window” — he makes you believe they’re right there in front of him, prompting a reverie, reminding him of very specific regrets.  When he recalls “the sunburned hands” he used to hold, back in a lost summer of lost love, you sense he’s remembering the exact way they felt in his hands.

The falling of leaves in autumn is a familiar metaphor, a cliché, but not in Dylan’s rendition of the song — he summons up an image of real leaves that will eventually have to be raked into piles and burned.