I’ve met a lot of young people who are fascinated with the era they see depicted on “Mad Men.” No song better epitomizes the era than this swaggering 1960s version of Pennies from Heaven by singing legend Frank Sinatra with jazz legend Count Basie and his Orchestra. The genesis was a “historical” album Sinatra did in 1962 with Basie. The two had long admired each other and that was their first team-up recording, at the height of the era depicted in “Mad Men.”
The first cut on that album was this song, the coolest, most swaggering jazz version of Pennies from Heaven. Quintessential Mad Men era. Except on the original album Sintra ends the song with a long note.
Some years later, in a November 1981 Sinatra TV special, they did it in live performance, and Sinatra was more relaxed, doing it with even more 60s swagger. Watch him: he looks like a character out of Mad Men. And also watch for how evident it is that Sinatra and Basie liked each other. Watch from beginning to end to see a rendition of a song that symbolizes the attitude of a whole era:
FOOTNOTE: I wore the original CD out that had this number. I’ve just ordered (not arrived yet) a remasted CD that contains the two classic Reprise studio sessions that Sinatra-Basie did. This song (the original rendition of it) is on it. Here’s the CD on the market now:
Joe Gandelman is a former fulltime journalist who freelanced in India, Spain, Bangladesh and Cypress writing for publications such as the Christian Science Monitor and Newsweek. He also did radio reports from Madrid for NPR’s All Things Considered. He has worked on two U.S. newspapers and quit the news biz in 1990 to go into entertainment. He also has written for The Week and several online publications, did a column for Cagle Cartoons Syndicate and has appeared on CNN.