Here's a guy that decided to ask for a Million Dollars on Youtube:

And here is the last video he posted: (Edit: there was a bleeped out swear word in the video, so I removed it.)

Here is an article talking about what happened next.

From The Article:

he says he has found a benefactor and has produced a notarized letter from that millionaire's lawyer.
Just because Rowin asked -- and for no particular reason.
Why does he want the money? "It would be awesome," said Rowin.
What will he do with the money? "I might go on a trip," he said.
Rowin said he received a phone call from the would-be philanthropist:
"Hi Craig, Benjamin, I was hoping to catch you in person," the caller said. "I want to talk about how to make you a millionaire."
Rowin has said he will reveal the man's last name when he collects the check at a Feb. 2 performance of the "Upright Citizens Brigade Theatre" in Manhattan.

It is a good reminder that it never hurts to ask... Because the worst thing that anyone can tell you is no!