Damon Salvatore

Rebelled by leaving the Confederacy during the time of the Civil War
1864: Shot by his father while attempting to save Katherine from him;
Had vampire blood in his system, forced to feed on a human by his brother, became a vampire
Spent centuries, killing humans & tormenting his brother
1950s: Captured & experimented on by the Augustine society, escaped 5 years later
2009: Returned to Mystic Falls to free Katherine, discovered she never loved him
Grew closer to his brother, worked together to protect Elena & her friends
Injected with the Ripper Virus, turned into an Augustine Vampire, cured shortly after
2014: Car exploded, resurrected into the 1994 Prison World, trapped with Bonnie until she managed to free them
2015: Stabbed with the Phoenix Sword, resurrected by Bonnie
2016: Staked by Alaric Saltzman, resurrected by Arcadius
2017: Siphoned of magic by Kai Parker, resurrected by Arcadius
Tried to sacrifice himself to save Mystic Falls, stopped by Stefan & given the Cure;
Spent the rest of his human life with Elena, lived a long and happy life together, died of natural causes