Here's my stupid story...
The first time I played Punch-Out was in an arcade. I was probably 6 years old. For some reason I thought I was controlling the other boxer, trying to keep the 'challenger' (whatever initials you entered at the beginning) from going through the ranks. So there's Glass Joe amazingly KO'ing this transparent green contender, and I'm thinking I'm the man while unwittingly getting my ass whooped.
Funny thing is, around the 5th time I played I couldn't manage to "lose." I went through 8 or 9 guys, playing like I'm supposed to be knocking out this green freak, thinking I suck ass because I can't seem to stop him, when in reality I was tearing shit up.
I've had experience that would qualify as more special, but that was undoubtedly my dumbest gaming moment.