5. Jason Bourne
It would not be anyones ideal scenario to wake up on a strange boat after being pulled from the ocean with a bullet wound and not knowing who you are, where you came from, and what you were doing there in the first place. However as long as you woke up with the set of skills that Jason Bourne possesses, you might call it a wash and be perfectly ok with it. Just think about this for a minute; most trained operatives go through years of grueling mental and physical training to become the elite spy, assassin, solider, and the like that they end up becoming. They know all the effort and sacrifice that went into the end result. They know just how lethal and dangerous they are. Now, think about how fantastic it must be to have no idea you ever lifted weights. To have no clue you ever trained with guns and weapons. To not be aware you ever learned how to think and act like a spy or that you ever learned to speak foreign languages, and just instinctually were able to beat the living snot out of those people who are coming after you for no apparent reason in your mind? It would be the ultimate holy shit what did I just do and more importantly how moment. It is a feeling that unfortunately no one but Jason Bourne knows. The quest for that feeling is the reason any guy out there would love to trade places with him regardless of the negative aspects and dangers that come along with not knowing your past.