Gears of War 2 (I think) with the Gary Jules version of Mad World certainly deserves a shout out. Probably already mentioned, but it was certainly a bit ahead of the curve with this.

His schtick grew old. I was a massive fan 10+ years ago when he was just a guy writing really witty stuff once or twice a week. He was a fan of the lovable loser Red Sox and wore his heart on his sleeve. Then the Boston teams started winning and he frankly became insufferable.