For his 14th album in a 32-year-long recording career, song satirist and accordionist Weird Al Yankovic has managed to do something marvelous, and even unique: he’s made his new collection, Mandatory Fun, featuring his twisted takes on popular songs from Pharrell Williams, Iggy Azalea and Lorde, into something as fresh as it funny. That’s not easy when every network, televised and on-line, hosts parodists of all stripes. Yes, it features Yankovic’s usual genre parodies—the skeletal punk of the Pixies, the slimy sensuality of Robin Thicke—and a polka medley of recent hits. Still, Mandatory Fun sounds like both the work of an old master and a comedy nubile just getting his feet wet. And for this, the ultimate self-proclaimed nerd now celebrated by hipster icons such as Pitchfork Media and Chris Hardwicke, winds up with his first entering-at-Number-One Billboard entity. I caught up to Yankovic two days before the illustrious honor and he seemed genuinely perplexed.

It’s more than likely in the next several day you’ll enter Billboard’s Number One spot for the very first time, and…

Gosh. Ahh. Don’t even say it. The fact that people are talking about this is so surreal, it boggles my mind. I don’t want to set myself up for a letdown. It’s crazy to even think about it. And it’s not as if I’d be disappointed with the Number Two spot or anything really in the Top Ten. Even that is a huge deal. It’s beyond comprehension.

I know. It’s like asking Meryl Streep what she’s thinking about her next Oscar nod. OK, so have you ever wanted to do this straight? Make music that doesn’t benefit from satire?

Not really. People have asked me, beyond comedy, if I’m harboring any secret vision to do a “serious” album. I look around and see that there are enough people doing unfunny music already. Funny is how my brain is wired in the first place. I do this because I love it. I honestly enjoy comedy and making music and I’ve always been a little twisted, so mine is the perfect job. I’ve certainly known musical acts over the course of my life who had that first novelty hit, then when they got people’s attention, dropped what they thought of as “their real music,” my serious oeuvre, but that’s not me. This is what I do.

I ask not because I’m waiting for “your more serious record” but because you are a damned accomplished accordionist. You could have been the Art Van Damme/Myron Floren of your time.

I always knew, though, that if I ever got truly serious about playing the accordion I might be very in demand on the bar mitzvah circuit. Or at the very least, make a comfortable living playing Italian weddings. It wound up being more fun to make my own path.

Are you necessarily a fan of—do you like each of the artists—that you satirize? You seem so invested, say, on the new album doing takes on Lorde and Pixies, but I just thought that you might not always dig everything that you satirize.

Not necessarily, but I do say that I normally pick songs that I like because I’ll wind up having to live with them for the rest of my life, whether it’s through their recording or even, possibly, in live performance. For that reason alone, I pick songs that won’t drive me crazy, although the primary reason for choosing each song is whether a song is popular and whether I can come up with a funny enough idea for it.

Outside of video ideas that you can parody – for example your “Fat” version of Michael Jackson’s “Bad”—what first element gets you about a song? What’s the initial spark that makes you go, Ahhh, I can do something here?

It’s honestly an almost undefinable quality. It’s a musical or lyrical…thing…that just jumps out at you the moment you hear it. I can parody something and do it in a generic way. You can do that with almost everything. But the best parodies come from songs that have the truest signature about them. It also helps if the original artist is a huge personality so that you have characteristics you can exaggerate and caricature. Obviously, a song’s popularity is a strong asset. If it stays on the charts for ten weeks, that’s a pretty good indication that people are ready for parody.

That video shot with you and Iggy Azelea on TMZ. She says she’s psyched to get an enormous royalty fee, but TMZ—which is run by a lawyer—states that parodists do not have to pay up. What’s wrong there?

Everything. I make deals with all the artists I work with. They keep the publishing money, and we split the writer’s money, so she absolutely will make money. TMZ says she’s mistaken, that she obviously doesn’t know copyright law. She is as entitled as the other artists are, to fair songwriting royalties.

So once again, TMZ is wrong.

Imagine that!

Between Funny or Die, and a world of YouTube videos, have you had to up your game? I don’t think of you as competitive, but certainly this glut has made it harder to find the funny beyond the overcrowding in its most unique and timely form.

It makes it more of a challenge, let me put it that way. I think that it’s really healthy that all of these humor-themed portals on the Internet have created a level playing field for comedians. I wish there was YouTube when I was growing up. I had the Dr. Demento Show so that was my entrée into show business. Nowadays, kids are free to upload anything they like, and if they show real talent and are unique, people will pay attention. That’s a nice way to start a career. It makes my job just a little more difficult and challenging because I will never again be the only person to do a parody of any given hit song. Then again, I wasn’t the first to do it, so that’s fair. It just means that I have to keep at it, up my game, and work harder. Also, it behooves me not to pick the most obvious idea. If there is one truly apparent theme for a song, you can bet a thousand different comedians have already done it.

Hence, you turning “Blurred Lines” into “Word Crimes” and dictionary dilemmas, and Lorde’s “Royals” into “Foil” and a soliloquy on food wrap techniques. Curious as to what place in your mind Demento still holds. You don’t hear from him as much, but he’s out there.

Gosh, he changed my life in a very real and direct way. If it hadn’t have been for Dr. Demento, I guarantee you that I would not be in the music business right now. I would have either been an architect—which is what I got my degree in—or I would have some day job that I wouldn’t have enjoyed a fraction as much as the career I have now. Demento played my stuff on his radio show

Then nationally syndicated.

Yes. When I was recording in my bedroom with my accordion and a cassette tape deck. I can’t think of anybody else in the universe who would have given a kid like me a second look. But there was Dr. Demento and he gave me encouragement and airplay and kept at it until I had developed a cult following.

You mentioned getting that architecture degree. When was the last time that you had an opportunity to do anything with it?

Well, we’re currently remodeling our den, so I had to draw up some floor plans for it. That’s about it. Oh, and I still print pretty neatly. They really drum that into you, good printing skills. It’s gotten a little sloppy over the years, but I still have definably architectural lettering.

What does your 11-year-old daughter think of your music?

We haven’t let her listen to it yet. We want to shield her from all that. No… kidding. She’s always been a fan, and she’s always enjoyed what I do ever since she was a toddler. She enjoys the new album, and she’s one of the first people I run my stuff through. She’s very grounded, and doesn’t get overly excited by the trappings of pop culture. She also doesn’t roll her eyes in the way that you’d expect somebody of her age might if their dad was Weird Al. She’s a good sounding board. In fact, I went to her when I was wondering if I should be doing Iggy Azalea. At the time “Fancy” was going up the charts, I thought that there might be something to do with that song. I asked my daughter if they were talking about Iggy at school and my daughter said “not so much.” I waited another week, and asked the same question, and my daughter was like “Oh yeah. That’s all the kids are talking about.” That’s when I realized that we had reached the tipping point, and I should do my parody.

I noticed that you’ve been all over social media pushing the new album’s agenda. Are you good with 140 characters or is Twitter just a necessary business evil?

No, I actually enjoy it. I’m obsessed with social media. Having said that, I got dragged into it kicking and screaming. It seemed like a real time suck at first. Once I got into it, I loved it because it allowed me genuine communication and interaction with my  fans on a minute by minute basis. It also allows me closer contact to my peers and friends in the comedy community. It’s really opened things up for me.

That’s funny you say that because you always seemed to be, without pounding out a cliché, an island unto yourself—your own genre and best connection to your own world, far apart form other comedians and connections. Suddenly, you’re on Chris Hardwicke’s @ Midnight as if you’re best friends and fellow comedians seem to genuinely love you. What changed?

I’m suddenly feeling that, and it’s odd. I guess part of that comes form the fact that I wasn’t easy to pigeonhole. Back when there was such a thing as a record store, you weren’t sure if you would find my stuff in the rock section or the comedy section or the novelty section. Nobody knew what to do with me and I fell between the cracks; never completely accepted in the comedy community or the music community. As time went on, and by my sheer will of force or force of will, I’ve managed to hang around, and am now accepted by both worlds. And that’s a wonderful, warm feeling.

I know you’ve had issues—from management mainly—with using Lady Gaga music, and more recently with Pharrell’s people until you happened to deal with the artists themselves. Is this often the case?

These situations are the exception to the rule. In all fairness, I think that my management was talking to the wrong people when it came to Pharrell. After I spoke with him, I got connected to the right person who couldn’t have been nicer. I won’t say how and with whom I did this, but Pharrell was the nicest, sweetest person and honored by my wanting to parody his songs.

What’s the biggest difference between directing your own videos as you do normally and those of artists such as the Black Crowes, Hanson and Ben Folds which you’ve tackled?

It’s more fun to spend other people’s money.

Is there ever a moment when you’re storyboarding where you’ve had one definitive idea that somehow just didn’t work, and the process had to be changed? I’m making you sound like a fly-by-the-seat-of-your-pants improvisationalist, but…

Not really, because I do all of my editing in the concept stage. I generate a lot of possible variations on a theme, and I never sign off unless I am absolutely convinced of the strength of those ideas. Once those ideas are down, I commit one hundred percent. I don’t believe that I’ve ever gotten halfway through a song I was performing, and gone, “Wait. No. this isn’t working.” I give it everything I have from the very start.

What was the logic behind the barrage of eight videos from Mandatory Fun at one time?

I wanted to make an event of the release of the album. Since MTV no longer stands for “music television,”they’re not thinking about me and I’m not thinking about them. The only way to work and live is on the Internet. I knew that I had to look to the online community to market this record. I learned that it has a really quick turnover, especially for comedy. Things go viral and get popular really fast, then die off and become old news the next day. What’s next? I figured that I could stay relevant for an entire week if I filmed and came out with a video every single day. I didn’t know that it would work—maybe people would tire of me. It would either backfire or have a snowball effect and it looks as if it had the latter. People were extremely excited the first day, the next day, and so on, which is amazing. I hadn’t done this before, and the success it had went beyond my wildest expectations.

If you give up on comedy or architecture, you’d make a marvelous advertising  executive. You’re at the end of a single 32-year-long, 14 album record contract, and I know you’re trying to figure what you might do next. Got anything for me?

People think it’s hyperbole or a joke when I talk about that contract, but no, I signed in 1982 and I’ve fulfilled my contract. And  I have to say that, truly, I don’t know for sure what to do. I’m not retiring, which some people thought. I really don’t think I’m going to be doing any more albums, not conventional ones at least. I have said like things like this before and the headline came out “WEIRD AL RETIRING.” I’m not retiring of my own free will. I just don’t think—and I feel strange saying this knowing that my album is going to be my most successful album on the charts yet—that albums are the best, most intelligent and efficient way to get my material out there. I’m trying to be topical and timely, and if  I release all twelve songs at once, it’s a challenge to keep each and every one of them fresh. I’d rather just put ideas out as I think of them, which would make me more competitive with the amateurs on YouTube who drop videos as soon as they think of it.