Historic Comedic Convergence

Back before he was the proud bearer of all things "truthiness," Stephen Colbert was an established comedian with a knack for improv. By 1999, he was already a veteran of Chicago's famous Second City troupe, working as an understudy for fellow Daily Show alum Steve Carell. It made sense, then, that the stars would align and that Colbert would land a one-episode stint on the classic ABC show Whose Line is it Anyway? 

At that point, he was already a few years into his stint with Jon Stewart and Co., so he wasn't a complete unknown. The best part about this story is that selected segments are up, for your viewing pleasure, on YouTube.

Here, he does a strangely-convincing German accent in a foreign film dub game.

Demonstrating a devastating combination of literacy and articulation, he's the perfect "Dating Game" contestant. (Apologies in advance for the random, mid-screen text.)

He got the chance to play my personal favorite WLIIA game, "Props."

His turn in "Scene to Rap" catches Wayne Brady a little off-guard. I can't decide if it looks better or worse this way.