If more people were making and uploading videos to the internet in 1999, this bridge would've been crossed long ago: Michael Bolton acts as the character Michael Bolton in Mike Judge's Office Space. Yep, the disaffected co-worker who loves rap music, and hates being associated with Bolton's name—and the emotional wrecking ball lameness that's association with his music—is now played by the ballad singer himself in a Funny or Die sketch.
Compare the real Bolton's beaten-down-by-life take (above) to the original trying-to-be-cool Michael Bolton (played by David Herman) below. What do they have in common? They're only able to cut loose—and be the true Michael Bolton—when they're listening to Scarface.