Atreyu - Storm to Pass (I feel like their buzz single was so much better.
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Colbie Caillat - The Little Things (Her label should've picked a song like Magic, Oxygen, or One Fine Wire, because I feel like all of her singles from that era sounded the same.)
JoJo - How To Touch A Girl (Just slaughtered the entire era, when This Time, her first potential #1, was sitting right there)
Linkin Park - Leave Out All The Rest (It's a solid album track, but just not appropriate as a single... No More Sorrow = Underrated masterpiece)
Nas - Umm... he didn't even promote his first single, which, by the way, was the best rap song of that year), so he really didn't deserve a second one, even though that album was flawless.
Lupe Fiasco - Hip-Hop Saved My Life (Massive let-down, when the gold mine called Hi-Definition was sitting two songs up on the tracklisting)
Kanye West - Basically the entire 808s & Heartbreak era, post-Heartless. He kept releasing video after video and it got really messy.
Lil Wayne - His mistake was not providing a follow-up to Mrs. Officer. He could've gotten at least two more Top 20 hits from Tha Carter III. And don't even get me started on Rebirth, he was doomed from the beginning.