Acclaimed Flop: "My December" is this. Critically acclaimed, very left wing lyrically, extremely personal and literal. Wasn't that successful and her companies disown it to a degree.
Black Sheep Hit: Inverted with "Because of You". She re-recorded the song with Reba McEntire and released it to country radio. She's made the country charts again in 2010 with the Jason Aldean duet "Don't You Wanna Stay".
And a third time with a remix of "Mr. Know It All".
And a fourth with "Don't Rush".
Creator Breakdown: It could be argued that most of her music leans this way, with very few love songs and happy songs in general. My December being the greatest example of this type of thing.