Yup, I've sung "I Feel Pretty" and "Gee, Officer Krupke" to him. Of course, this is in addition to the 70-something prank calls I've done:
"Congratulations, Mr. Rene Sance! You've been selected to take a survey and enter for a chance to win $3000! Now, please call us back with your answer to this question:
What do you think of greenhouse gases?
Call to enter for your chance to win $3000 dollars!
One will enter, none will win. This contest is void in the United States, Canada, and every other country for that matter."
"Congratulations, Miss Clara Net! You've been chosen to be an anchorwoman on the Cearadactylus Network! Please come to orientation on June 32 at 5:00. Bring your own mic."
"YO! Aengus! You know who this is! Gimme a beat J.T.!
Hey Hey You You!
I don't like your girlfriend!
No Way No Way!
Think you need a new one.
...And that is all."
"And I was like, 'O. M. G.' You totally took my boyfriend. And she was like, 'No. Way.' And I was like, 'Way.' And she was like 'I didn't take your boyfriend.' And I was like, 'Yeah you did!' And she was like, 'I don't want to date your stupid boyfriend.' And I was like, 'No. Way. You did not just call my boyfriend stupid' And she was like 'Way.' So I was like, 'OMG.'"