The debate likely will rage forever on whether or not Frank Sinatra was a jazz singer. But you’ll get no argument from anyone that Sinatra was one of the greatest performers of modern pop songs, especially those from the 20th century’s Great American Songbook.

Sinatra’s career was so long — spanning seven decades — and his recorded output so vast that it’s hard to come up with his five best albums. It has to be done from a purely personal point of view. But for those who are diving into Sinatra’s catalogue for the first time or returning to some old favourites, you can’t go wrong with these five standout releases.