Edgar Allen Poe
Poe had abysmal luck from the start. His father left him, then his mother died, all before he was three. His family was dispersed, and Poe ended up living with a wealthy tobacco merchant named John Allan in Richmond, Virginia. He was obsessed with poetry early on, and already had enough work to fill a book by the time he was 13. But his foster family did not support his ambitions, and Poe actually had to burn his own furniture to keep warm in his college days while he chased his dream. By the time he had returned to Richmond, his financee had become engaged to another man. Welcome to Poe's life: the definition of one thing after another.
After falling out with his foster family, Poe tried to reconnect with his biological relatives in Baltimore, only to be robbed by them. John Allan died during this time, and left Poe out of his will despite including an illegitimate child who John Allan had never even met! OUCH. The only upside was that he continued publishing his exquisitely macabre work, though he was barely making ends meet. Just as he had started to receive some degree of fame with "The Raven," his wife Virginia died, which completely devastated him. He followed her two years later, dying under extremely mysterious circumstances which are still disputed today. Though it's fitting that this legendary Gothic writer had such a dark and turbulent life, we sure wish we could send a letter back in time to him to let him know how beloved he is today.