Most people have a band they really liked and hoped would succeed, only to see them basically flounder in relative obscurity.
Greenwheel was possibly my favorite band late in my High School career. I saw them live I think 5 times, and every time was awesome.
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Another band I really liked, although I only got to see live once, was Far Too Jones
Both bands I've mentioned are alt-rock bands in the genre of Hoobastank or Puddle of Mudd, they certainly can't be accused of being super original, but I thought they both performed a well explored genre to perfection. You can certainly say they were probably trying to break into a market that was already flooded with similar sounding (though IMO inferior) bands.
One of Greenwheel's songs did end up as a top 10 hit, just not with them singing it LOL. Melissa Ethridge covered their song Breathe.
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ttt
Adopted son of Lord Sephiroth, Youngest sibling of Pent uP Rage, Prarara the Great, Nerwen Carnesîr, TB666 and, Boudicca. In the great Family of the Black Prince
There was this R&B/Jazz band from Toronto, Jacksoul, they were well acclaimed in Canada and were doing pretty well until the lead singer got in a car crash and coma for a few years, then died not long after he woke up. Terrible.