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How did Al get his start in the music business?

As a teenager, Al began sending homemade tapes of his songs to Dr. Demento, a nationally syndicated disc jockey known for playing comedy and novelty music. Demento found a certain charm in the accordion-powered ditties that Al recorded on a cheap cassette player in his own bedroom, and gave him his first airplay. By the time Al graduated from college, he not only had a modest cult following from the good Doctor's radio show, but he also had a couple of nationally-released singles ("My Bologna" and "Another One Rides The Bus"). In 1982 he signed a deal with Scotti Bros. Records, who went on to release all of his albums through Bad Hair Day (1996). Volcano Records eventually bought Scotti Bros. Records, issuing Running With Scissors and Poodle Hat, and re-releasing Al's entire catalog on the Volcano/Way Moby label.

Does Al get permission to do his parodies?

Al does get permission from the original writers of the songs that he parodies. While the law supports his ability to parody without permission, he feels it's important to maintain the relationships that he's built with artists and writers over the years. Plus, Al wants to make sure that he gets his songwriter credit (as writer of new lyrics) as well as his rightful share of the royalties.
What do the original artists think of the parodies?

Most artists are genuinely flattered and consider it an honor to have Weird Al parody their work. Some groups (including Nirvana) claim that they didn't realize that they had really "made it" until Weird Al did a parody of them!

What about Coolio? I heard that he was upset with Al about "Amish Paradise."

That was a very unfortunate case of misunderstanding between Al's people and Coolio's people. Short version of the story: Al recorded "Amish Paradise" after being told by his record label that Coolio had given his permission for the parody. When Al's album came out, Coolio publicly contended that he had never given his blessing, and that he was in fact very offended by the song. To this day we’re not exactly sure who got their facts wrong, but Al sincerely apologizes to Coolio for the misunderstanding.