The System - S1-E2
Stupidity: The plot hinges on the fact that even Frank Marley's most trusted man would doubt him because of his actions, but he and Marley counted the money together; he should know that Marley was right and the amount declared was not lower than the actual money deposited. Instead, he is fooled like everyone else by the extra 25K$ planted by the IMF team. Their plan can't work unless he is oblivious and/or forgetful.
Emohawk - Polymorph II - S6-E4
Stupidity: On the walk back to Starbug, the Emohawk jumps on Lister's head to disguise itself as Lister's hat, but it leaves itself in its natural form whilst the crew continue to walk. The Emohawk is supposed to be disguising itself to fool the crew into making them think it is any everyday object. The Emohawk eventually changes into Lister's hat, but leaving itself in its natural form even for just a small amount of time could blow its cover. (00:18:15)