This piano-laden song was the third single taken from neo soul musician Maxwell's fourth studio album, BLACKsummers'night. Like several other tracks on the record, it has a melancholic vibe. Maxwell told The Idolator that this reflected the ending of a relationship in his personal life. He explained: "Not that 'black' is synonymous with dark, bad or messed up things, [but] it conveys a certain somber feeling. That's kind of why the record deals with break up… real life affects your art. I found myself in a situation where my expectations were not met. Not that that person was messed up or anything—sometimes reality comes and checks you, and I kind of got a reality check. But it inspired a lot of creativity for the record. Something that was kind of painful actually made my work more important and interesting to people in the world, so I'm pleased about that."
This was Maxwell's fifth Adult R&B chart-topper and his third in succession following "Pretty Wings" and "Bad Habits." When the song reached pole position Maxwell became the first solo male to link three consecutive #1s. The only other artist to achieve this feat is Alicia Keys who has done so twice.
On his VH1 Storytellers appearance, Maxwell explained: "Fistful of Tears was definitely inspired by the war. I hate that we're fighting, I can't wait for the troops to come back. The fact that we're fighting a religious war is crazy to me. Everyone should believe whatever they want to believe in - just don't mess with me. That's what spawned it, but it's also trying to express to someone that's so beautiful and so amazing how great they are when they can't see how great they are."
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