'Weird Al' Yankovic

Hawaiian shirt, canvas shoes and (until 1997) glasses
Frequently makes reference to the number 27
Writes songs about food, television series and romances that end in bloodshed
Performs polka style medleys of songs that have no connection with each other, as if randomly chosen
Often features a celebrity guest appearance in his music videos (such as Florence Henderson in "Amish Paradise", Ruth Buzzi and Pat Boone in "Gump" and Dick Van Patten in "Smells Like Nirvana")

When he asked Nirvana for permission to parody "Smells Like Teen Spirit", their first question was, "Will it be about food?". When Weird Al explained that "Smells Like Nirvana" would be about how nobody could understand their singing, they agreed that it sounded funny and granted permission.
Said he knew he had made it as a famous musician when he went to a party, saw Paul McCartney and before he could introduce himself to the former Beatle, McCartney recognized him and said, "Hey! It's Weird Al!".
Graduated valedictorian from Lynwood High School at the tender age of 16. Moreover, Weird Al was one of the most popular kids in his class. He also claims to have started a club called "The Volcano Worshippers", so he could get his picture onto even more pages in the school yearbook. Famous alumni from his school include Kevin Costner, Mark Spitz, Suge Knight, Fred Gwynne, etc.
He was offered the opening spot for the European leg of Michael Jackson's "Bad" tour. However, he was involved in the production of his movie UHF (1989) at the time, and respectfully declined.
Another artist to have denied parody permission is Paul McCartney. Weird Al wrote a parody of "Live and Let Die" called "Chicken Pot Pie", but McCartney (a staunch vegetarian) denied permission. As a result, Weird Al has never released the song, but has performed it in concert.

[on a 1999 episode of Behind the Music (1997), answering a question about (then) being unmarried. He is now married and has a daughter] My parents are like, "Well, he's almost 40, lives in Los Angeles, and he's unmarried. You know what that means!".
A lot of artists have really been supportive over the years.
I'm still a geek on the inside, that's the important thing.
How can you get bored if the audience is cheering and laughing at something you're doing?
As my father used to tell me, the only true sign of success in life is being able to do for a living that which makes you happy.