Cap’s greatest love was his WW2 comrade, Peggy Carter. The tragedy that Cap was never able to live out the life that he had imagined spending with Peggy is perhaps the saddest part of Captain America’s history in comics. This song is a great choice for Steve’s playlist, and you’ll see why from the lyrics. “Well, our captain fell in love, with a lady like a dove. Her name that she had was pretty Peggy-O.” It doesn’t get more perfect than that. Too bad Cap had to wait more than 50 years to hear this song, because he would have loved to share a moment with Peggy while they listened along.