29. Mason Lockwood
Hot Uncle Mason pushed Damon one step too far, and ended up with his heart ripped from his chest…all because he loved Katherine.
28. Tyler's pack of hybrids
When Klaus found out his hybrids all conspired with Tyler behind his back to break their sire bond to him, he got his revenge in the only way he knows how: by brutally murdering them out in the woods. Merry Christmas?
27. Pearl
John Gilbert couldn't allow Pearl to live so he staked her as she was on her way out of town, leaving her daughter Anna all alone. Watching Anna break down over seeing her mother's corpse? If you didn't shed a tear, you're as soulless as John Gilbert.
26. Anna
While it was sad to see Anna die, we were crying all of the happy tears when she was finally reunited with her mother Pearl on the Other Side.
25. Esther Mikaelson's first death
For thousands of years, everyone thought Mikael killed his own wife because she had an affair with a werewolf. But she was really murdered by her own son Klaus, kicking off a bloody, thousand-year grudge between the siblings and their father.
24. Sheila "Grams" Bennett
Bonnie's grandma died twice for her, first when their spell to open the tomb was too much for them to handle, and again on the Other Side to make sure that Bonnie was "taken care of" when the Other Side collapsed. She lived a full life and ensured her granddaughter's safety as her final act, so even though we didn't want to say goodbye to Grams, we knew it was time.
23. Jeremy's third human death
This one wasn't as sad as his first two deaths, since he volunteered to have Bonnie stop his heart and restart it to perform the dessication spell on Klaus. There was a moment where we all freaked out and thought Bonnie's spell to bring him back didn't work though, so thanks for the mini heart attack, TVD!
22. Tyler/Julian
Markos wanted to make sure his Traveler spell was still in effect around Mystic Falls, so he pushed the Passenger possessing Tyler's body over the town line and watched as Julian's magic was stripped, leaving Tyler as a human, dead with a broken neck. He managed to escape the Other Side crumbling and came back to life as a human who has yet to trigger the werewolf curse by the end of the same episode, though, so we weren't in mourning for too long.
21. Nadia Petrova
Katherine's daughter just wanted to get to know her mother, but all she got was a bite from a werewolf! After Tyler bit her, she died in her mother's arms.
20. Vicki's final, ghost death
Vicki sacrifices herself as the Other Side crumbles so her brother Matty can get back to his body in time. Now that's a beautiful way to send off a fan-favorite character!
19. Enzo
Stefan accidentally killed Enzo in self-defense and to protect Elena from Enzo's revenge, and yes, it was an accident. Stefan had his hand around Enzo's heart, and Enzo yanked himself backwards, knowing that Damon would want revenge on Stefan for killing him. Yeah, this vamp was definitely a villain but we loved his snark and sarcasm so much that we didn't want to see him go! Thankfully, he stuck around as a (pesky) ghost until he managed to escape the Other Side and come back to life a few episodes later.
18. Stefan
We never like Julian, the traveler who was possessing Tyler's body, and he proved our suspicions right when ripped out Stefan's heart in order to stop the traveler spell from spreading outside of Mystic Falls and killing every supernatural creature in the world. We could barely believe our eyes watching Stefan dessicate on the ground. We didn't have to mourn losing his hero hair for long, though, since he came back from the Other Side in the next episode!
17. Katherine Pierce
We loved sassy Katherine, but when it came time to say goodbye, it would have been a lot sadder if she hadn't had a last minute change of heart and stole Elena's body for a frustrating few episodes prolonging her real death! But the huge twist that showed Katherine not peacefully moving on to the Other Side but instead getting pulled into some dark and violent afterlife was shocking and fun surprise...and let's be honest, totally deserved!
16. Grayson and Miranda Gilbert
The death of Elena and Jeremy's parents signaled the end of their supernatural-free lives, which is certainly sad enough on its own. But couple that with the fact that Elena's father sacrificed his own life and made Stefan save Elena over him as their car was sinking? Just absolutely heartbreaking.
15. Jeremy's fourth human death
When Katherine offered up little Gilbert's neck to Silas and the immortal snapped his neck, we all thought this was really it for Jeremy. Since he was a supernatural creature—a hunter—now, that meant his ring wouldn't bring him back, but Elena spent a full episode in denial about that. Until, that is, his body started to smell (ew) and she was forced to shut off her humanity switch to cope with losing her brother. Bonnie eventually sacrificed herself to bring Jeremy back.
14. Rose
After suffering horribly from a werewolf bite, Damon showed his emotional side by giving Rose a "day in the sun" before mercy-killing her. We, along with Elena, fell a little bit more in love with Damon after watching that selfless and noble act.
13. Carol Lockwood
Watching Klaus drown Tyler's mother in the middle of the town square for revenge while a hauntingly beautiful Christmas carol played in the background? Chills.
12. Alaric's first, human death
After he confronts Damon about killing his wife Isobel, Alaric tries to stake Damon, who—in self-defense—ends up sticking the pointy end into Alaric instead. But thank goodness for that mysterious ring that protects from supernatural death, because for the first time, we witnessed a human coming back to life. We were completely shocked...and eternally grateful that we still got to have Matt Davis on our TV screens!
11. Lexi
Back when Damon was a full-fledged villain, he staked Lexi in front of Sheriff Forbes to cover up the fact that he was a vampire. And seeing as how Lexi was Stefan's best friend and "sober counselor," this was just unforgiveable. Yeah, we're still mad about it.
10. Damon
Although Elena couldn't hear him, Damon's final goodbye to Elena was so heartbreakingly perfect. He was ready to meet his end as the Other Side was crumbling and he was trapped, because he lived a happy and full life, all thanks to Elena loving him. But we were with Elena: don't go, Damon!
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9. Bonnie's second (and final?) death
After Qetsiyah transferred the Other Side anchor to Bonnie, she was able to exist on both sides of the living and the dead. But when Markos came back from the Other Side, he set off a chain of events that led to the Other Side crumbling for good, trapping Bonnie and Damon in an unknown place. The image of longtime rivals Bonnie and Damon holding hands as they met their fate? Pretty much soul crushing.
8. Bonnie's first death
Bonnie sacrificed her own life to bring Jeremy back from the dead. The most heartbreaking part of Bonnie's death? She refused to let Jeremy tell anyone else she died, pretty much making her sacrifice thankless. She let all her friends spend months thinking she was just on vacation when she was really standing next to them as a ghost, living vicariously and depressingly through their lives.
7. Jeremy's first real death
Sheriff Forbes, who can do no wrong, made the biggest mistake when she accidentally shot and killed Jeremy. Since his supernatural ring doesn't protect him from normal, human deaths, Bonnie had to beg the spirits to bring him back no matter what, not knowing that he'll come back with the ability to talk to ghosts…including his ex-girlfriends. You don't know ex-girlfriend drama until you've had to deal with dead ex-girlfriend drama.
6. Vicki Donovan
The first major death of the show was also one of the saddest, as Matty's little sister couldn't deal with becoming a vampire. After she attacked Jeremy and Elena, the Salvatores were forced to put her down. This was the first clue that fans shouldn't get attached to any characters, even series regulars, because literally no one is safe from death on The Vampire Diaries.