Don’t be intimidated by the Orwellian directive behind Weird Al Yankovic’s new album title, Mandatory Fun. The listening experience is much more pleasurable than it sounds, which is not surprising for a musician who has become the definitive musical satirist of our generation. Over the last three decades, he’s parodied everyone from Michael Jackson to Taylor Swift, starred in two TV shows — one of which included a theme song about Al living in the sewer with a hamster — and, perhaps most impressively, made playing the accordion cool (you’re welcome, Accordion USA News). On top of that, Yankovic is also a world-class music-video artist, and with Mandatory Fun, he’ll team up with Funny or Die, Nerdist, College Humor, and others to debut eight music videos in eight days. Prior to the release of the new album, Weird Al rang up Vulture to reminisce about shooting a few of his earlier videos, from his debut, “Ricky,” all the way up to “Perform This Way.”

“Ricky”

“That was done in 1983. It was when my first album came out, which was right after MTV debuted. The thing about MTV was it was a 24-hour music-video channel that started back when people weren’t making music videos, so they needed product to fill the pipeline. So it was relatively easy to get played on MTV because they would play anything that wasn’t overtly horrible. The ‘Ricky’ video had very low production value. We made it for a couple thousand dollars. We shot it in somebody’s house in the San Fernando Valley. It really was lacking in not only production but in proper preparation. At one point I was supposed to be shaking maracas, and nobody had remembered to bring maracas, so I grabbed the closest thing that resembled maracas, which was a bowling pin [laughs]. So at one point in the video you see me shaking a bowling pin as fast as I can, hoping that nobody would realize.”

“I Lost on Jeopardy”

“I not only got to work with Don Pardo and Art Fleming, who were in the original Jeopardy show from the ‘60s, but Greg Kihn, the original artist who did ‘Jeopardy’ — he makes a cameo appearance at the end. But what a lot of people don’t realize, when I did ‘I Lost on Jeopardy,’ Jeopardy was not on the air; that was a retro song about the game show that Merv Griffin had created that was popular in the ‘60s when I was a kid. And the fact that I did that parody I’m told made Merv Griffin consider doing the show again. So I think the parody had something to do with the fact that Jeopardy went back on the air. We put the [cameo] request out, and Art Fleming and Don Pardo agreed to do it. They were perfect sports about it. Art Fleming showed up on the set and was more than happy to make goofy faces and play along, and Don Pardo just killed it. So I was very fortunate that they were both so game about the whole thing.”

“Like a Surgeon”

“We shot that in an actual hospital that had closed down and was mostly used as a hospital set. My biggest memory was we actually had a live lion on the set for those scenes where there’s a lion roaming the hallway. At that point we lost a lot of extras because they were saying, ‘You know, my day rate is not worth this’ [laughs]. It was just fun to be writhing around on a hospital gurney in a music video because I normally do that in my everyday life, so it was nice to be able to do that in public for a change.”

“Christmas at Ground Zero”

“It was a simple enough video to direct. Ninety-eight percent of that video is basically stock-footage clips from public-domain Cold War footage. There was really only one shot at the end, which was easy enough for me to direct. That was also a video the record label did not want to make, because for some reason they thought a Christmas song about nuclear annihilation wouldn’t really play during the holidays. But I wanted to have a Christmas song out, so I funded the video myself; it wasn’t that expensive.”

“Fat”

“The very first time that I saw the ‘Bad’ video on TV, I had the epiphany that ‘Fat’ was a pretty obvious parody idea for me. Since I had already done ‘Eat It,’ it seemed like a natural sequel. As I was watching the video, I just imagined an 800-pound version of myself trying to get through the turnstiles on a subway, and I thought before the video was over, okay, I am doing this. I have to do this. Thankfully, Michael Jackson let me use his subway set, which had not been struck yet; it was still on a soundstage in Culver City. So we were able to shoot there. I was able to hire plus-size dancers, which you’d think you wouldn’t be able to find pretty readily, but in Los Angeles, you can find virtually anything you need. I also remember that these were late-’80s special effects. If I were to do the ‘Fat’ video now, it would be a fairly simple job in CGI to have my face expand from normal to huge. Back then, that wasn’t a viable option, so I had to have latex bladders glued to my cheeks and I had a team of my visual-effects people blowing through tubes, which ran down my shirt and my pants and onto the floor. They blew my face up with these tubes. It was pretty old-school, but it looked great. [The suit] wasn’t uncomfortable. Half of it you weren’t even seeing. I was like swimming around in that suit. So you kind of got the gist of what I was doing. But it was difficult to move quickly. I would turn and then the suit would turn like a half-second later.”

“Smells Like Nirvana”

“We got the original janitor, who was actually [‘Smells Like Teen Spirit’ director] Samuel Bayer’s plumber, oddly enough. And we cast the same guy in my video. But we also used some of the same cheerleaders, we used a number of the same audience members. They seemed a little reluctant at first because they loved Nirvana, as did I, and they didn’t want to be part of mocking the group that they loved. But they found out early on that it was a loving tribute and it was all done in good fun and it was under the blessing of the band, so they got into it very quickly. I found out [Tony Hawk was an extra in the video] after the fact. He tweeted that a couple of years ago, which kind of blew my mind. And then I looked at the video and was like, Yeah, I think that’s him right there. So that was a nice little tidbit. [The Dick Van Patten cameo] was sort of a last-minute thing. We were looking around for a random celebrity to have in the video and I forget who we had been approaching, but I found out at the last minute that they weren’t available. And I think it was an hour before we were set to shoot it and I was like, ‘Does anybody know any celebrities?’ And somebody was like, ‘I know somebody who knows Dick Van Patten.’ And I said, ‘Great! Let’s get Dick Van Patten!’ And an hour later he was on the set. Then he became kind of our good-luck charm. We used him in several videos after that as the random celebrity cameo.”

“Jurassic Park”

“That was all stop-motion animation, and that was done by Scott Nordlund and Mark Osborne. Basically they took a house in the Valley and they converted it into an animation studio, and every room in the house had a different set where they were working with clay models. They got all their friends and they worked nonstop for a month. They cranked out just a wonderful stop-motion animated video, which wound up getting nominated for a Grammy. When I pick my animators, I pick them based on their talents and their genius and I try not to micromanage. I prefer that they run ideas by me first so that I’m not caught off-guard. But if they want me to be involved, I am happy to be involved in every step of the way, or if they want to go off into a room somewhere and show me what they’ve come up with, then that’s fine, too.”

“Bedrock Anthem”

“It was shot in the desert and we were able to pinpoint the exact spot in the desert where [the Red Hot Chili Peppers] shot their original video. It was really bizarre. We found the general area and then we found like, ‘Okay, that’s the bush he was singing in front of.’ And it was hot. It wasn’t a comfortable shoot. We were there shooting with glitter paint all over our bodies and trying not to get sunstroke. I also remember that I had these fake tattoos. I think I had Pebbles and Wilma on the side of my arm in Sharpie pen. And then two days later, when the ink came off, it was sort of like a reverse tattoo, because I had gotten sunburnt around the Sharpie. I guess the Sharpie had some natural sunscreen in it.”

“Amish Paradise”

“As people know in Hollywood, if you can’t get Michelle Pfeiffer for a gig, you get Florence Henderson. And she was wonderful. It was great to have Florence on the set. She was so into it. She was sucking in her cheeks like Michelle Pfeiffer. Also, I got to work with my parents and a bunch of my relatives because we were trying to keep the costs down. I got to use them for extras, as Amish people. It was probably the scariest moment ever on a music-video set for me, because the part where the barn door falls down, that was not an effect, that was a real thing. And it wasn’t just wood, because they were scared that if it was just wood, it might torque a little bit and not hit the mark. It had to land exactly where it was supposed to land or else it might hit me right in the head. So that barn door was not just wood; it was reinforced with steel on the inside. So really, if that door had made contact with me at all, I’d instantly be dead. So that was another of those one-take things. I am going to get through this and try not to be scared out of my mind, and if I survive this then we’ve got the shot. And it fell down and I didn’t die and we were done. If this had been done in the present-day, I am sure we would have done some wonderful green-screen to make it look real, but at the time it was like, ‘Oh, let’s just risk my life. That will be quicker.’”

“It’s All About the Pentiums”

“Drew Carey plays Mase in that. I was proud of that video. I kind of thought that was going to get more airplay than it did. Because it had the hot video women, it had Drew Carey and Emo Philips and really good production values. Which is why when ‘White and Nerdy’ came out a few years later, I thought, Well, this is sort of the same thing. It has the same subject matter and I can’t imagine this is going to do a whole lot better, but let’s give this a shot. And that wound up being my best hit of all time. So I guess I was maybe a little ahead of the curve when I did ‘Pentiums,’ because that seemed to be when nerd culture was peaking.”

“White and Nerdy”

“If you’re going to do a video called ‘White and Nerdy,’ Donny Osmond is your go-to cameo. And he was unbelievable. You never know when you ask a celebrity to do a cameo how invested they’re going to be in it. Donny was flying in from Salt Lake City, and I didn’t know if he was just going to go through the motions, but he had the song memorized, he had his moves down, he nailed it. In fact, if you go to YouTube, I have a video up called ‘White and Nerdy (Take #1),’ which is literally the first complete take of the video with me and Donny Osmond. I had no idea what he was going to do. I said, ‘Okay, Donny, let’s just go through it once and I will see what you’re doing and I’ll give you notes.’ And that was what he did. It was insane. Every take was as good or better than that one. He really brought it in that one. I wish the whole video could have been me and Donny Osmond because he had so many great moves.

“I’ve known Seth [Green, who also had a cameo,] for many years, and I knew he had a lot of props that we could use, and he was nice enough to come in and do a quick cameo. You know, people have been just discovering this, but Key and Peele are in that video as the gangsters in the car. It’s fun for me to watch my Twitter feed every couple days, someone will say, ‘Did you know Key and Peele are in the White and Nerdy video?!’

“[It was also the first time I rode a Segway.] I own a Segway now, but I think at the time they charged me $500 to rent the Segway, which I thought was a little ridiculous. And I said, ‘You know, we are going to use this in a video and I think that you would enjoy the exposure.’ But they came back to us and said, ‘We don’t want our product associated with anything white and nerdy.’ I was like ‘Uh, a little too late for that, guys!’”

“Perform This Way”

“That was, and perhaps will remain, my last big-budget music video. The record label paid for that — or actually, I did. I paid for it out of my royalties, but they fronted the money. And it was kind of pricey because we went through a lot of costumes and wardrobe and it was a very involved and complicated video shoot. It was a challenge, and we were able to pull it off, and I am very happy with the way it turned out. It’s sort of the end of an era. I don’t think I will be doing something like that again. The record labels, they don’t have as much disposable income as they used to. I worked with a stylist [on the video], and I tried to articulate exactly what I was going for, and she presented me with a lot of great options. So it was just a matter of narrowing down. It wasn’t a problem for me. I tend to work with very talented people, and they make me look good. A lot of [the costumes] were just things that were found. We’re talking about costume shops that basically have the whole history of Hollywood in them, so there have been a lot of bizarre things from other shows over the years. I think very little had to be created for that. It was just discovered and repurposed.”

The History Behind 12 Great Weird Al Videos