That's a tough one! I guess I picked Gollum because he lived in misery for hundreds of years - although I feel worse for Frodo. As the quote says "how do you pick up the threads of an old life?" - he was probably never the same again after his adventure and that has always made me sad

Gollum obviously cause i wouldnt want to be a drug adict for 500 years

Frodo, because I would not want to have to take the Ring of Power to Mount Doom....especially with all those Black Riders on the road.