First: In first grade I asked my dad why we couldn't just share our money with my poorer classmates and he said it was because that's communism and it's bad.

Second: I got in an argument with a girl in my middle school because I said Che was a murderer. I read it in an AIM chat room and just went with it... I was a dumb kid but I was really cute so people put up with me.

Third: In high school there was this kid who everyone knew as the communist and he wore the shirt you're referencing in the OP. He invited me to an illicit game of capture the flag at the governor's mansion and we protected our Soviet flag while trying to capture the black flag that the local anarchist group had brought. Just some friendly leftist in-fighting.

Edit: also Command and Conquer: Red Alert 1, 2 and Yuri's Revenge.