When I Lost You
Frank Sinatra; Gordon Jenkins & His Orchestra Lyrics

When Sinatra sings "When I Lost You," he's channeling heartbreak and the accompanying sense of loss. The opening lines suggest that he's lost everything that ever made him happy or hopeful. All the sunshine, the roses, the blue skies, the rainbows, and the morning dew have vanished, leaving nothing but gloom. Most significantly, he's lost the angel who gave him summer and winter, a metaphor for a significant other who was with him through all the seasons of life. Her departure turned everything he treasured into sorrow, as joy was replaced by angst.

As Sinatra lingers on the line "I lost the angel," it becomes more and more clear that this loss is the most painful, as it sets off the chain reaction of his other losses. The line "the whole winter too" emphasizes that the separation was prolonged and that the pain continued for months. When Sinatra repeats the final two lines, "I lost the gladness that turned into sadness when I lost you," his voice is filled with emotion, conveying the depth of his suffering.