By today’s standards, Frank Sinatra comes off as obtuse and dusty. The image of a tuxedoed old man bobbing across a stage crooning sanitized jazz standards smacks more of mealy-mouthed nostalgia than anything else, and nostalgia is by its nature almost always conservative.

Indeed, in 1985 Sinatra received the Presidential Medal of Freedom from Ronald Reagan — whom he supported. Conferring the medal on Sinatra, Reagan declared: “His love of country, his generosity for those less fortunate, make him one of our most remarkable and distinguished Americans.”

It’s a politico-artistic association that, however cringeworthy, maintains an internal logic. Two old white men shaking hands; your uber-conservative grandfather sings Reagan’s praises and Sinatra’s songs. It would be easy then to merely shrug at the fact that Sinatra would have turned one hundred this month.