But times have changed. While it’s always been tough to make a living in pop music, but you can make the case that today it’s virtually impossible, with the prevalence of free online music sharing and the pennies-on-the-dollar royalties artists get when their music is actually purchased.

Like just about every other business, the music recording industry has been revolutionized by online sharing and changing consumer demand. Attempts to crack down on free online sharing resulted in the Napster case—seven years of litigation between the recording industry and an Internet startup involving copyright violations,

The irony is that since then, free online music sharing has become ubiquitous – as simple as cutting and pasting from YouTube and transferring that audio file to your MP3.

So how does Weird Al make a living? His Internet strategy is to partner with popular web content sites like Funny or Die, College Humor, Yahoo and Nerdist, which pay to produce his videos: "They're all looking for content and I'm looking for a video so we partner and it's a win-win situation."

In turn, Weird Al reaps the benefits by using those videos, which have cost him nothing, as “commercials for the album,” which he hopes sells big.

Weird Al is facing the end of an era. He has been locked into an album deal since 1982, and his current release marks the end of that contract. But instead of hanging up his accordion, he's learning to adapt to the new reality of Internet marketing and sales.

Going forward, his business model will focus on releasing singles to keep his material fresh and topical, and continuing to partner with online content sites to sell his work.

Song parodies aren’t insurance, but insurance people can learn a lot from Weird Al. In a recent NPR interview, he muses on the fact that song parodies by amateurs are a dime a dozen on YouTube today, and now that he no longer has a record contract, he has to compete with all of them.

He recognizes that the beauty and the curse of the Internet is that content goes viral and is forgotten in the blink of an eye. The advertisers who keep the web content sites afloat are focused on page views and other metrics, and stale material doesn’t get hits. By ditching albums for singles, Weird Al can stay on top of the rapidly shifting terrain of pop music—generating content that gets views, keeps websites and their advertisers happy, and spurs download sales of his own music.

He also knows that promoting his material can’t stop with the Internet. Building from the loyal fan base he’s developed over the years, he tours regularly, giving face time to his constituents.

And although he knows there’s plenty of cheap competition out there looking to steal his thunder, Weird Al abides.

From the NPR interview:

If you had asked me 30 years ago if I'd still be doing it today, I'd say that's pretty unlikely. But I love doing this. I can't imagine a job I'd rather have. I love comedy, I love music. I'm sure people will let me know when it's time to hang up the accordion and call it quits, but it's a lot of fun for me still, and as long as people don't mind, I'll keep doing it.