41. 21 by Adele 
For the tragicomic single "Rolling in the Deep" alone, Adele's 21 deserves a spot on this list. Almost scarily descriptive about the dreadful catch-22 of doing what's right for the mind but leaves your heart in pain, "Rolling in the Deep" became the quintessential song for the one that got away. The rest of 21 also harkened to the time of officially coming of age (18 ain't cutting it if you can't drink!), and every song in its idyllic, bluesy-jazz composition soared for wisdom. Sometimes being 21 isn't all fun and games. There's some suffering along the way.