We've got a player who's a specialist.
He made so much mistakes at Ars Magica we're still laugh. Example: after a king of gnome-like faeries gave us 50 Terram virtus (a huge load of raw magical power), but adding that he wanted this debt to be repayed: "What a bitch !" ...
Another time, our mages were discussing about a problem with evil feys in a nearby forest, whose presence was making every plant less fertile -- to the point that a famine was threatening. He say "I'll meditate one quarter of hour outside". Rather than meditate, he go investigate the cave of the evil feys. Its is strongly inclined (something like 60°), and wet, thus slippery. It's also dark, so he tries to cast a light spell. He botches it, and is blinded by his spell. Nothing wrong with poor luck. However, despite being blinded, he choose to enter the cave nonetheless. After some hard encounters with stalactites and stalagmites, he crawl outside. The morning after, we see him crawling back to the covenant, clothes tattered, face burnt, and with small wounds everywhere.
With another mage, while we where before a labyrinth where a mage has been trapped in a stasis field, the gatekeeper explains: "only the bravest and most pious of the knights could deliver the wizard from the labyrinth [unfortunately, said knight died in our trip to the place -- precisely because of that character, who've failed a check and fall in an avalanch, and the knight hushed to rescue her, only to be taken also by the avalanch. We've been able to rescue the mage, but not the knight.]. Furthermore, if one of you enter this place, know that your magic won't help you, as all magic is stripped from those who enter." The frail mageress: "I'll try." Luckily for her, the first encounter of the labyrinth was a very slow skeleton, who did minimal damage on its attack. So, she could crawl back to safety, her belly half-open in two by an axe blow.
In our first D&D adventure, our level 1 characters were investigating a so-called haunted house (who was in fact haunted only by illusions and slavers who found in the house's cave a passage to an underdark caravan trail). While we're in the house, discussing of what we should do, his halfling rogue take a torch and say "you're boring with your endless talk, I'll check the cave alone". Luckily for him, the orcs below were slavers, not cannibal, so we found him alive but unconscious in a little cage latter.
Some quotes of that player:
"Yes, it's a trap, but since we know it's a trap, we can be cautious and we won't have any trouble"
He is also a specialist of confused explanations. In that same game, we were tasked with retrieving dwarves for a dwarvish organization. It turned out that this organization were the villain of the story, bent on killing all dwarves that have some individualistic mindset (in that setting, most dwarves are almost like robots, because of their origin as a slave race: they are made to work, and the only thing that please them is working; however some dwarves are free-willed; and this organization considered free-willed dwarves as an aberration, ironically they were all themselves free-willed dwarves...). So, we found one of these "renegade" dwarves in the guise of human, polymorphed by an evil wizard against nearly all his money. The dwarves thought to be well hidden this way, but the polymorphing had the side effect of making him age too fast. Like 1 year older each day.
Anyway, our character got arrested and put in jail, and to lessen his sentence, he want to reveal things to the authorities.
"I can talk to you about the Purifier"
"What's that"
"They're dwarves who've a blast at blasting dwarves. They kill dwarves."
"Huh... Well, can you be more explicit ? Give names ?"
"Yes, there's <someone> who have seen a wizard to make himself old, and..."
And he's like that everytime...
