
one of my icons is francis albert sinatra. sinatra was the original king of cool. he’s that rare combination of a man’s man and a ladies’ man. i discovered his music in 8th grade when the columbia record club accidentally sent me a copy of his album reprise: the very good years. i was hooked the minute i heard “the way you look tonight.” since then i’ve been obsessed with the legend of frank sinatra. he truly lived his life his way. we should all be so lucky.
many of you casual sinatra fans own one of his greatest records. that’s a great place to start, but there’s no need to stop there. i’ve got a friend who’s been asking me to introduce him to more sinatra, so consider this your introduction. here are my three favorite sinatra albums and the ones you should start with:

a swingin’ affair!: it’s tough to say one of these 3 albums is better than the others, but i listen to a swingin’ affair! more than the rest. i tend to gravitate towards the uptempo stuff and nelson riddle’s arrangements are as good as it gets here. if you only have the cash for one of these, start with this one. it’s considered the follow up to the album below, but i think it’s better.

songs for swingin’ lovers: a lot of people put songs for swingin’ lovers at the top of their list and for good reason. it was released a year before a swingin’ affair and features sinatra at his most confident (according to experts). it’s another sinatra and riddle collaboration that breaths new life into pop standards such as “pennies from heaven” and “i’ve got you under my skin.”

in the wee small hours: many consider in the wee small hours to be the first concept album. the idea was to make an album featuring only ballads about lost love and isolation (apparently it was a direct response to his separation from ava gardner). i dare you to make it through the whole thing without weeping. recommended if you’ve just broken up with your girlfriend and are having a cocktail and a sulk.
what to buy next: sinatra sings for only the lonely, songs for young lovers/swing easy, come fly with me