It didnt happen with me but I bet that someone will mention the Barrel from Sonic 3 Carnival level. You know, the one where you couldnt figure out that you need to press up and down.
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FUCK that barrel. God.
You know, I actually got past it once by timing my jumps to "stomp" it down far enough that I could go through the opening (or so that it shot me up high enough to jump to the ledge, forgot which mechanic that puzzle operated on).
I lost countless lives to the 10-minute level time limit thanks to that red-and-white checkerboard cocksucker.
Also, X-Men for Genesis. Mojo's Crunch. "Reset the system!!11!!!one" Lame.
Jam it back in, in the dark.