The Self-Made Man: Weird Al Yankovic

This week’s Self Made Man is an entertainer, but not one who grew up poor and sang/played himself rich. No, this man’s story is a little weirder, which makes sense because he’s Weird Al Yankovic.

Al isn’t someone you’d think of when making a list of entrepreneurs, and he probably doesn’t consider himself to be one, but he’s turned song parodies—the last resort of every hack comedian and morning radio DJ on the planet—into such a cottage industry for himself that they’re associated with his name first and foremost now. No one else can try and go mainstream with song parodies because they would immediately be accused of biting off Al’s thing.

Wait, let me rephrase that. Anyone else who tries to make a career out of song parodies will be accused of ripping off Weird Al.

Al first started writing song parodies as a nerdy teenager in Lynwood, California. Inspired by the comedy songs and obscurities he heard on Dr. Demento’s radio show, Al would arrange and play stuff on his accordion and record on a crappy tape recorder in his bedroom. He would also play at open mics around town, which is hilarious when you stop and think about what coffeehouse open mics were like in the mid-1970s. I’m picturing lots of beardos in earth toned sweaters or hiking shorts trying to be James Taylor, and then this goofy kid comes up with his accordion and sings something about food.

Anyway, Al eventually sent some of his home recordings to Dr. Demento, who liked them enough to play them a lot on his radio show and add Al to his stage show. Al, who by this point had a drummer to help him keep the beat steady, got a manager who convinced him to put a full band together and take his act on the road, thinking that Al was an enthusiastic enough performer to make an otherwise-corny act work.

Al was also quick to get on MTV during its early days when the network was starved for content, and his funny videos and solid arrangements proved that there was significant talent behind the novelty.

It helps that Al is a true showman who has performed thousands of live shows across the continental United States, and isn’t afraid to play state fairs and other gigs that other performers wouldn’t touch. He’s also put out plenty of albums to further prove how strong his work ethic is.

Weird Al’s father, a WWII veteran, often told him that “the key to success [is] doing for a living whatever makes you happy,” and Al’s career is a testament to that wisdom. Al’s career is also a testament to dedication. He found something he liked to do even though it was uncool, and then made it cool through his efforts. That kind of goal-oriented individualism is one of the main tenets of being an entrepreneur, and we here at TSB think Weird Al Yankovic is a fine example of it.

Here’s a fun video about Weird Al’s career courtesy of WatchMojo.com.