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Bree (Gina Torres)
We loved her because: She was the coolest. Bree, a former flame of Damon's, owned a cool bar that served cool underage kids cool beer, which made Elena so much cooler. She also had the guts to betray Damon and stand up for Lexi (more on that later).
We lost her because: As much as we appreciate those guts... they did her in. She tried to call in vampire backup to avenge Lexi's death, but once Damon was onto her, he ripped her heart out. Literally.