Supernatural: The Most Heartbreaking Deaths, Ranked 1 Dean Winchester (S15, EP 20 "Carry On") 2 Bobby Singer (S7, EP 10 "Death's Door") ... 3 Castiel (S15, EP 19 "Inherit the Earth") ... 4 Sam Winchester (S15, EP 20 "Carry On") ... 5 Charlie Bradbury (S10, EP 21 "Dark Dynasty") ... 6 Jo and Ellen Harvelle (S5, EP 10 "Abandon All Hope") ... #3: Dean's Hell Confession\n\n Although Dean was able to resist for 30 years, he eventually gave in and spent the last decade inflicting pain on others. Brilliantly acted, the monologue Dean delivers is absolutely heartbreaking and would easily be the saddest Dean moment in the series & if not for the next entry.
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