As a child I almost always cheered for the “bad” guy. When watching He-Man, I wanted Skeletor to win; I could not stand Tweety Bird or Jerry Mouse, or the Road Runner, for that matter; I always preferred the “mean” cats and the “wild” coyote. This is also why I never really enjoyed James Bond except in those films where the special-agent showed his vulnerable side, such as On her Majesty's Secret Service (Lazenby's first and only foray) and the more recent Casino Royale.
Why? Because I find the good guys generally boring. They are too perfect and not all that human in my view, so I cannot fully relate to them nor find them interesting in any discernible way. At least, the bad guys have some weaknesses - if you want to call being evil a weakness, that is - and more importantly, they more often than not lose out.
This sympathy for those who show signs of weakness can be extended to various areas of life. For example, Nietzsche's idea of the Superhuman, the Übermensch, I find too bland. What is the point of such perfection since there is nothing to improve upon. With the exception of art perhaps, perfection means death and stagnation since what is already perfect cannot -- and has no need for -- change. On the other hand, flaws make the person endearing, strange as it may sound.
On the flip side those who claim to have no weaknesses are blatant liars or hypocrites. Take womanizers, for instance. They (or so they claim) always get the girls and “play” them as if they were their toy or piano. The word rejection is not in their repertoire, and they (supposedly) laugh in the face of failure.
Such people generally speaking strike me as dishonest. I believe half of them may be actually gay, while the other half may be simply deluding themselves. In reality, they must be unhappy or feel unfulfilled deep inside and would most likely prefer a constant and life-long companion instead of another pointless “one-night stand.”
So who would be heroes to me? I must say I do like Batman and Optimus Prime, but in general I prefer those heroes that have an Achilles' heel, such as, well, Achilles or Siegfried with his soft (mortal) spot on his back. They may be strong, but they are not invincible; moreover, they are mortal. This is something that I can identify with more than those who can survive anything and where there is very little at stake for them.
Now at the point of sounding a bit pretentious, my heroes are those who turn what is seen as weakness into strength. That is good old Mahatma, the frail little man who stood up against the powerful and mighty British army and still won. It is Jesus whose cheek already read turned the other side to receive the next blow like a man! Yes, those who are “soft” (the gentle in gentleman) and nonviolent, often mistakenly perceived as weak, are the real heroes out there. So don't tell your friend to suck it up like a man because it is their so-called weakness that makes them heroic, at least in my mind.
And to add here, one of my soft spots are the downtrodden and misunderstood, especially those who suffer from unrequited love. The ones who don't get the girl will at least - consolation prize - have my full sympathy. I can, from previous personal experience, relate to them; their failure in romance makes them so much more heroic and turns them into a living poet regardless if they turn to writing or not.
But to be perfectly honest, my sympathy for so-called losers may have a self-serving bias. When you see somebody who is worse off than you, there is a certain kind of comfort. Not in a blatant finger-pointing, “ha-ha” manner of course. One may feel superior, but it is also strangely reassuring since all things considered, we may be slightly better off than them.
However, I like to believe that the “poor losers” strike a compassionate chord within me. Not included are those who are losers but think or try to convince themselves that they are very special; they elicit mostly laughter. Yet when it comes to the genuine losers, their humanity makes them not only vulnerable but gives them a touch of honesty and dignity. For those I wish the best and hope that despite not having succeeded in their endeavor, they will find the incentive and push to get it right the next time around.