Love Stinks: Billboard’s 30 Biggest Heartbreak Hits

Not everyone equates Valentine’s Day with red hearts and roses. For those that have not found cupid to be so kind, February 14 can be a reminder that sometimes, love really can suck. This fact has not been lost on pop musicians; for every whimsical song about love’s dizzying highs, there’s a woeful tune referencing its heartbreaking lows.

These are the 30 biggest heartbreak songs ever recorded. Ranked by their performance on the Billboard Hot 100 chart from its inception in 1958 to Feb 11, 2012, each song is included based on its lyrical content. Every song celebrates the darker side of love: heartaches, breakups, lying, cheating, unhealthy obsessions and general relationship dysfunction. Crank up your computer and get ready for a good cry:

25.“Love Takes Time”
Mariah Carey
1990
Most Heartbreaking Lyric: “Couldn’t see that I was blind to let you go? / I can’t escape the pain inside / Cause love takes time / I don’t wanna be here, I don’t wanna be here alone.”

1.“We Belong Together”
Mariah Carey
2005
Most Heartbreaking Lyric: “The pain reflected in this song ain’t even half of what I’m feeling inside. / I need you, need you back in my life, baby. / We belong together.”

See the complete list here.