It’s safe to say that you probably underestimate “Weird Al” Yankovic, or maybe at least you did to some degree before 2014. Once derided as “Mad for the ears,” he’s now three decades into the most lucrative career to combine music and comedy since the days of black-and-white film. His song parodies (with respective videos) helped usher several different generations of adolescents into a contemporary pop education prematurely, skewering Michael Jackson, Madonna, Nirvana, R. Kelly and so forth, all the way up to Chamillionaire and Pharrell. He didn’t back down when pop changed lanes and introduced rappers, grunge, Papa Roach, you name it. Naysayers may believe the 55-year-old satirist to have the world’s easiest job, while he and his band actually take the pains to recreate the most popular songs in the Western world (and their state-of-the-art productions) from scratch — and that’s only after tracking down the original artists’ permission.

His efforts to stay current have paid off: This year’s Mandatory Fun was his first No. 1 album, and comedy’s first chart-topping debut on Billboard’s Top 200 ever. Helped by eight straight days of new YouTube premieres, from the Lorde-themed “Foil” to the expert Pixies swipe “First World Problems,” many of these are the most relatable songs from a guy who’s more known for cheap punch lines (see: “Fat”). After all, who hasn’t met someone who Instagrams every meal they’ve had, or never lets you forget a favor they did for you, as in the “Happy” revamp “Tacky?” Yankovic spoke to SPIN via email about a year so successful that it was briefly rumored he would headline the 2015 Super Bowl halftime show.

I know you had “Handy” prepared under a tight deadline. Which artists have said no to a parody, especially if it was half-written already?

Oh, I hate to focus on the negative — and it’s so rare that an artist says no, especially these days. Since you asked, I will say that Prince did turn me down on a number of occasions — but truthfully it’s been a couple decades since I’ve contacted him, so who knows, maybe he’s developed a sense of humor by now! I don’t write any actual lyrics before asking an artist’s permission, on the off chance that he or she doesn’t want me to do the parody. Thankfully, I’ve got a pretty decent track record at this point, so almost without exception an artist will sign off on a parody based on the title and concept alone.

Do you have any originals you’ve written that don’t end up on “Weird Al” albums or aren’t suited to comedy, and are just sitting on a hard drive somewhere?

First of all, there are no “serious” “Weird Al” songs in a vault somewhere. My brain isn’t wired that way, and by my estimation there are enough “serious” songs in the world already. Fact is, there really aren’t even any unreleased funny “Weird Al” songs either. I hate wasted effort, so I’m not one of those recording artists that writes a hundred songs, records 40 of them, and then picks the best dozen for the album. I try to do all my editing in the concept stage. I’ll spend a lot of time figuring out what my best 12 ideas are, and then I’ll commit to those ideas completely. I’ll write 12 songs, record 12 songs, and release 12 songs. I don’t leave myself the option of producing something that’s not good enough.

There’s an almost political humility about Mandatory Fun: “Tacky,” “First World Problems,” “Mission Statement,” and, if you stretch a little, “Lame Claim to Fame” all complain about really relatable experiences, which is obviously important to finding them funny. But more than in your past work, these feel like checks and balances people might really encounter.

That wasn’t any kind of conscious decision, but I can see where some people might start connecting the dots and finding a theme. I’d say most of these songs employ a songwriting device which I believe Randy Newman refers to as the “untrustworthy narrator.” I’m obviously playing characters in these songs that are comically flawed in some way. Sometimes they think or do things that I would find abhorrent. It alternately amuses and horrifies me when fans (or even critics) infer that I’m writing these songs from some sort of personal perspective, or that these songs are somehow autobiographical. I mean, I freely admit that a song like “White & Nerdy” comes dangerously close to being autobiographical, but that character is still a bit of an exaggeration.

Have you ever parodied a song that you flat-out don’t like, only because the parody that popped into your head was too good to not use?

My personal opinion of a song has very little to do with whether or not I’ll decide to parody it — that decision is based solely on the popularity of the song, and whether or not I can manage to come up with a funny enough idea for it. Having said that, I do tend to pick songs that I actually like, because I realize I may end up playing them on stage for years — possibly the rest of my life. And by the way, I don’t really hate any music. I certainly prefer some genres or artists over others, but if I hear something that I personally don’t find appealing, I just say… “Well, that’s not for me. I’m not that artist’s target fan base.” I’ve never gotten all ’90s-indie-record-store clerk on anybody. I’ve never understood or related to people that despise any kind of music. I can appreciate pretty much anything.

Has anyone pretty much begged you to parody them and you weren’t feeling it?

Certainly not “begged,” but now and then I’ll bump into an artist at an awards show or some event, and he or she will offhandedly ask, “Hey, when are you going to do one of my songs?” I never know whether they’re being serious or just trying to make light conversation.

You ask permission for song parodies but not style parodies. Has anyone ever given you feedback on a style parody of them?

A few times I’ve done pastiches of musicians who were nice enough to come into the studio and actually play on my track! Ben Folds is an old friend, and he rocked the piano on my Ben Folds Five soundalike “Why Does This Always Happen to Me.” Similarly, Taylor Hanson played on my Hanson style parody “If That Isn’t Love.” As far as the new album goes, I’m friends with Frank Black, so I was able to surprise him with my Pixies takeoff “First World Problems” — thankfully, he liked it! And my drummer Bermuda [Schwartz] knows the guys in Southern Culture on the Skids and says they got a kick out of “Lame Claim To Fame.” Oh, and speaking of artists asking me to do a parody — I bumped into Graham Nash a couple years ago when we were both in New York doing publicity, and the first thing he said to me was, “So when are you going to get around to doing a parody of [Crosby Stills and Nash’s] ‘Suite: Judy Blue Eyes?'” I assume he was joking around, but as it turned out, I had just finished recording my CSNY-inspired song “Mission Statement,” so I was able to whip out my iPhone and play it for him — instant request!

Was 2014 the best year of your life?

I have to be careful answering this question because I recently did a Diane Sawyer interview, and the pull-quote was “I’ve been doing the same thing for 30 years, and all of a sudden I’m having the best week of my life!” And naturally my wife goes, “Oh, this is the best week of your life? Not the week you got married? Not the week your daughter was born?” So, I stand corrected. But in terms of my recording career, definitely. Hard to top this year. Pretty much impossible, actually.

What was the best thing about this year for you?

This is probably not going to come as a big surprise, but getting a No. 1 album is something I never dreamed would ever, ever happen. I figured it was out of the realm of possibility because historically, comedy records just don’t do that. Mandatory Fun is the first comedy album in history to debut at No. 1 on the Billboard [200], and it’s the first one in over 50 years to even reach No. 1. It’s still hard for me to wrap my head around that.

What was the worst thing about this year?

I don’t know — for me personally, it’s been a pretty darn good year! Hmm… I just had a root canal last month — I guess that wasn’t terribly fun, but it also really wasn’t all that bad. I’m not trying to duck the question, but off the top of my head I can’t really think of any personal tragedies or professional disappointments or public humiliations. Sorry… I’ll try to make up for it next year!

What do you wish you did more of this year?

I would have liked to spend more time on Maui. My family lives there part-time (mostly when my daughter isn’t in school) and we just love it. It’s such a magical place, and frankly it’s always a little depressing every time we have to leave.

What was the best thing you ate this year?

Oh man, that’s an extremely hard question to answer. I think I might have to say the black lentil daal at Bombay Palace. Even though I love Indian food, I’ve never been a huge daal fan — but theirs has this amazing, chocolatey texture and taste. It’s insanely good. We used them to cater an event and I got to bring home a huge container of leftover daal, so that’s pretty much all I ate for the next week or so. I may have burnt out on it just a little bit.

What’s the best rumor you heard about yourself this year?

Because of a popular fan-driven campaign, there was a rumor that I might be playing the Super Bowl next year. Of course I was extremely touched by the support of the fans and the media, but realistically I knew I’d never wind up on the NFL’s short list. Still, I have to say I was slightly relieved to find out the NFL wasn’t seriously considering me. The halftime performers are put under such intense public scrutiny, it’s brutal. It’s almost like being in politics — people’s emotions run very high. No matter who the performer is, there will be millions of people that love them, and millions more that hate them. I mean, I wouldn’t turn down the gig if it were offered to me — but I’m actually fine that there are a bunch of people saying, “Why isn’t Al playing the Super Bowl?” instead of “What’s this idiot doing playing the SuperBowl?”

Finally, how early it is appropriate to start playing Christmas music?

Personally, I think you should wait at least until after New Year’s Day.