Episode 5 of The World God Only Knows (Season 2) features an interesting cameo:
Not sure what kind of setting is in the game Keima is playing, though. Probably just random dialogue, but the cameo is incredibly unexpected. Where’s my D-Frag anime?! By the way, there’s almost no way this is coincidental, the likeness is spot-on:
And for those unfamiliar with this manga, Takao is the head of the computer game creator club (a.k.a. “chief” or 部長, which is the eroge character’s “name” in the 1st and 2nd screencaps).