In The Wee Small HoursFrank Sinatra
Of course this belongs on this list, there is no doubt about that. Sinatra was one of the most influential people in musical history after all. That being said, it hasn't aged the best. A full 50-minute album of songs about heartbreak? It starts to get pretty annoying after the third song of him singing about a girl leaving him. My brother in Christ, chill. I'm sure this would sound better at a cocktail party in the 50s. I don't think Frank anticipated people listening to this album through headphones, in front of their computer, working and drinking hot cocoa.