This version of the song was recorded for Columbia Records in 1949, before Sinatra had his amazing breakthrough as an expressive artist at Capitol Records, where he began his legendary collaboration with arranger Nelson Riddle.

At Columbia he was still using his longtime arranger Axel Stordahl, whose backing of Sinatra could be a little syrupy at times.

Still, you can sense here the beginnings of the almost conversational phrasing and emotional directness Sinatra brought to his great work in the Fifties.

Sinatra recorded the song twice more in the Sixties for his own label Reprise after he left Capitol.  One was a decent but uninspired duet with Rosemary Clooney, the other a dreadful, punched-up hipster version which doesn’t convey even a trace of genuine emotion.

Dylan has recorded “Some Enchanted Evening” for his new album of songs associated with Sinatra, due out next month.  Something tells me he’ll have taken his inspiration from Sinatra’s original version on Columbia.


Sinatra recorded this religious song in 1964.  It was the theme song of the movie The Cardinal (which marked the last screen appearance of Dorothy Gish).  Dylan has recorded it for his upcoming album of songs associated with Sinatra, Shadows In the Night.  You can stream Dylan’s version on NPR here.

Sinatra’s version, expertly sung as it is, is not convincing as as an expression of humility and faith.  Sinatra was capable of putting across religious songs convincingly, as his Capitol Christmas album shows, but his heart doesn’t seem to be in it here.  The somewhat bombastic orchestral arrangement doesn’t help.

Dylan’s version, with its creaky vocal and small-ensemble arrangement featuring steel guitar, is profound, heartbreaking.



. . . courtesy of my friend Laura Leivick.

The soundtrack album from the 1950 Broadway production, issued in 1954. Bob Dylan said that listening to Lotte Lenya’s performance of “Pirate Jenny” changed his idea of what a song could be.  You can see why — it’s startling and chilling and brilliant.

Click on the image to enlarge.