10.) Mass Effect 2
This is not exactly a shockingly inappropriate interroggation, but it was really entertaining to experience. Well, renegade playthroughs in Mass Effect is always memorable because you don't play by the rules and you're pretty much a jerk.
In Mass Effect 2, you have to interrogate Elias Kelham for Thane's loyalty mission. The cool part is you could either be the good or the bad cop in the interrogation. The Paragon and Spectre methods aren't really that exciting, so the most entertaining way to play this mission is Renegade style.
