At the beginning of the first episode of his Skyrim Let's Play he sings a rendition of Harry Partridge's Skyrim song that is surprisingly well done.
In part 49. After leaving the Thalmor Embassy, he accidently left one of the jewels for a quest there. Getting back into the Embassy is nearly impossible without mods, so he gets over the wall by exploiting a glitch where he uses his horse to jump over the wall! Also doubles as a Crowning Moment of Funny.
In the last episode of Deus Ex: Human Revolution: The Missing Link, Jesse is given a choice of saving either hundreds of innocent prisoners or the only person able to testify against the atrocities of Belltower from the poison gas the Big Bad unleashed. His kleptomaniac Hero tendencies pay off HUGE here, as he refuses both options and takes a third option. How? By deducing that the only possible third option would be in the only vent he never explored, due to being blocked by a crate he couldn't break. He then sacrifices the only shot of a Rocket Launcher he only received moments before to break the crate, enter the vent, discover the room where the gas is being distributed, and destroying it, savingeveryone.Holy shit!