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Am I the first person to feel strange calling you ‘weird’?”
John Mayer — bespectacled, grinning goofily, very much nerding out — is sitting across from “Weird Al” Yankovic, interviewing the Hawaiian shirt-clad parody music king, who is sitting across from him for his SiriusXM show, How’s Life With John Mayer.

“You can call me Al, like Paul Simon says,” Yankovic says with smile, before adding that the most normal thing about him is, probably, his pancreas.

It’s a funny quip, but also an understatement. Let’s just get this out of the way: “Weird Al” Yankovic is, beneath his accordion-playing, polka-loving surface, exceedingly normal. He likes long evening walks to get his steps in. He enjoys seeing movies and trying out new restaurants with his wife and daughter, who just graduated college. He grumbles good-naturedly about the ongoing renovation of his home in the Hollywood Hills. (“It’s going to look almost exactly the same as it did before, except it cost a fortune!”) The 65-year-old artist’s one attempt at rock star behavior, back in his early-’80s heyday, was comically un-vain: On a touring rider, he requested, in the spirit of Van Halen’s famed ban on brown M&M’S, “one really horrible Hawaiian shirt for every show I did.” (On that run, he did 200, and a collection that now extends to a storage unit somewhere in greater L.A. began.)

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Still, if not precisely weird, Yankovic is truly singular. His catalog can be divided into two types of songs: intricately crafted, meticulously arranged, hilarious yet never mean-spirited parodies of hits by acts ranging from Michael Jackson to Coolio to Nirvana to Lady Gaga, and original pastiches, for which he deep dives into artists’ catalogs to create songs that, with eerie accuracy, mimic the sounds and idiosyncrasies of those genre-spanning artists.

Between the two, he has accomplished feats usually reserved for the very artists he parodies. During each of the first four decades of his career, he has had entries on the Billboard Hot 100, and eight of his albums have reached the top 20 on the Billboard 200 — including his most recent studio release, 2014’s Mandatory Fun, which became his first No. 1 on the chart. He has won five Grammy Awards and an Emmy. Billboard estimates he has sold 12 million albums in the United States (based on RIAA certifications pre-1991 and Luminate data from 1991 on).

Incredibly, he’s done all this without ever changing his essential “Weird Al”-ness. “From day one, there was never even a discussion that would not be about following his singular vision,” says Jay Levey, Yankovic’s manager of 43 years and sometime creative collaborator (notably, they co-wrote the now nerd canon comedy UHF, which Levey also directed). “It’s hard to find any career where there’s literally no compromise, but we might be able to count on one hand the number of compromises he’s made in his career.”

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Sometimes, that’s meant turning down lucrative deals, like the $5 million beer endorsement that Yankovic passed on in 1990 because, he feared, the brand was “trying to make me into Joe Camel.” Many times, it’s meant standing up to record-label executives, like when, amid his “draconian” first album contract with Scotti Brothers (an indie then distributed by CBS), he was asked to shoot 10 music videos on a $30,000 budget simply because he’d proved he could do one for $3,000. (“I’m like, ‘No. No, I can’t!’ ”)

But just as often, it’s meant embracing an open-to-anything spirit that seems to almost always work out in his favor. Yankovic decided very early in his career to ask permission of any artist he parodied — not because the law required it (it doesn’t) but because he simply had no interest in making enemies. With very few exceptions, it turned out, the artists said yes, even supposedly impossible-to-convince ones like “American Pie” scribe Don McLean, who OK’d “The Saga Begins,” Yankovic’s 1999 parody that essentially ­summarizes the plot of Star Wars: Episode I — The Phantom Menace. “When I heard his version, I thought it was better than the original. The sound quality was superb,” says McLean, who calls Yankovic a “straight-ahead good boy” who “could be on Leave It to Beaver.”

Thanks to that combination of earnest good intentions, work ethic, backbone and obsession with quality, Yankovic finds himself in an unusual position today: He’s no novelty relic of the ’80s, but a truly cross-generational artist. In the past six years alone, he’s portrayed Rivers Cuomo in Weezer’s “Africa” music video, played accordion (and appeared in the video) for teen rock band The Linda Lindas’ 2024 single “Yo Me Estreso” and lip-synced dramatically in a tux in Clairo’s “Terrapin” video. “Growing up with his videos was a massive thing in my generation,” says Clairo, 26. “Back when YouTube was really simple, it really hit home for us in middle school to watch his parodies. He always knew how to draw people in.”

He and his team will prove just how true that still is when Yankovic heads out on the Bigger and Weirder Tour this summer. It’s his fastest-­selling, biggest-grossing tour yet, according to his agent, Wasserman Music’s Brad Goodman, and his biggest by other metrics, too: an eight-piece band (his largest yet) onstage; first-time venues bigger than any he’s played before, including New York’s Madison Square Garden and L.A.’s Kia Forum; a mini-Las Vegas residency (the tour will open June 13 with six sold-out nights at The Venetian); and stops both expected (Red Rocks Amphitheatre) and less so (Riot Fest) on the route. And the concert itself is a trademark Weird Al spectacle: part rock show, part revival tent, part Broadway musical, all “joy bomb,” as actor and longtime fan Andy Samberg puts it.

Whether it becomes a springboard for the next Weird Al era is anyone’s guess — including Yankovic himself. Right now, he has no further plans to release albums; and since Mandatory Fun arrived over a decade ago, he’s only sporadically released new music, most recently the 2024 “Polkamania!” single (the latest in his long-running series of madcap polka medleys, this one recapping the past decade’s pop highlights, all sung in Yankovic’s manic tenor). Around that time, his contract of roughly 20 years with Sony ended, and he decided not to renew with the label, or sign with anyone else.

“Nobody owns any piece of me,” he says, exhaling. “I’m at a point in my life where if something isn’t going to be fun or a pleasant experience, I have no problem saying no, even if it’s a lot of money or a lot of eyeballs. I can do literally whatever I feel like doing.”

Then again, for Yankovic, that’s always been true.

“When I was a kid, I used to fantasize about being the next Weird Al, like it’s a position he applied for and got,” says Lin-Manuel Miranda, a lifelong fan who’s now also friends with Yankovic. “And then you grow up and realize, ‘Oh, there’s only one of that guy.’ We’re not going to see ­another Weird Al.”

On an overcast April afternoon a few days after the Mayer taping, Yankovic meets me for lunch at Crossroads, a vegan spot in West Hollywood where, years ago, he ate his first Impossible Burger. He’s quick to jokingly note that he is not a member of the city’s “vegan elite” — still, as he walks in, a man walking a golden retriever stops his phone conversation to stare and declare, “It’s that Al Yanko-vich guy!”

Despite his talent for writing songs about junk food (“My Bologna,” “The White Stuff”) and the fact that he once consumed the world’s most ungodly snack, a Twinkie Dog, in UHF (watch and barf a little), he’s been vegan since the early ’90s.

Chalk it up to veganism, staying out of the sun (“I melt in direct sunlight”) or following the directions of his longtime hair stylist, Sean James, very well (he never blow-dries those famous ringlets, hence their eternally bouncy and well-defined nature), but Yankovic has an ageless quality that lends many of his fans to liken him to mythological figures. “He’s Santa Claus for nerds of a certain stripe,” Miranda says, a comparison Mayer had also made (as well as to Forrest Gump). His curls may be a little grayer, but his ultra-expressive face — acrobatic eyebrows in particular — reflects his eternal curiosity and up-for-anything-ness.

As we settle in for almond ricotta-stuffed zucchini blossoms and meatless bolognese, Yankovic is particularly animated recounting his previous weekend, when he made his latest surprise appearance: his Coachella debut. To close out its surreal set, the crew from the cult-favorite kids show Yo Gabba Gabba! brought out a cast of characters both human (Thundercat, Portugal. The Man’s John Gourley) and not so much (cartoon mascots like Sleestak, PuffnStuf and Duo the Duolingo owl) to sing “The Rainbow Connection” with its composer, Paul Williams — and, on lead vocals, Yankovic.

“I’ve had a pretty bizarre life, so it wasn’t like, so unusual,” Yankovic reflects. “But it was definitely a little bit of an out-of-body experience.” He admits that the “hey kids, let’s put on a show” energy was fun and that the invite wasn’t a total shock (having appeared on a season-three episode as an accordion-playing circus ringmaster, he’s tight with the Gabba group). Still, he speaks of such invites with a kind of humble awe.

“Nothing I’ve ever done was me thinking, ‘Boy, I hope kids discover this 40 years from now,’ ” he says. Starting in the ’80s, he released an album almost every year “because I was afraid I would be quickly forgotten. It was drilled into me: ‘You’re a comedy artist, you’re a novelty artist, you’re lucky if you’re a one hit-wonder — you’re not destined to have a long career.’ I wanted to grab that brass ring every time I went around.”

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Coming up concurrently with the birth of MTV, and savvily taking advantage of it, helped Yankovic snatch that ring. He had a keen ear for (and good taste in) hits at a time when, thanks to both MTV and top 40 radio’s prevalence, a monoculture reigned — and perhaps even more importantly, he knew the power of a viral video before such a thing existed.

Tweaking hits like Jackson’s “Beat It” (“Eat It”) and Madonna’s “Like a Virgin” (“Like a Surgeon”), Yankovic created new songs that, thanks to his painstaking re-creations of their arrangements, were immediately recognizable but rewarded repeated consumption — as did their accompanying videos, in which Yankovic demonstrated his incredible eye for detail and formidable acting chops. “MTV was on like video wallpaper in the background 24 hours a day,” he says of that time. “They were hungry for content, and I was anxious to give them content.”

Since then, Yankovic’s understanding of the promotional power of visuals has remained prescient — take when, leading up to Mandatory Fun’s arrival, he insisted on releasing a music video on YouTube each day (not all at once, as some advised) to whet fans’ appetites for the album. And his genre-agnostic approach to making music has proved ahead of its time, too. Before hip-hop was widely accepted as pop, he was especially drawn to rap. “A lot of pop songs are very repetitive,” he says. “How can I be funny in seven syllables, you know? But rap songs, I mean, it’s nothing but words, and it’s easy to craft jokes that way.”

Parodies like “Amish Paradise” (Coolio’s “Gangsta’s Paradise”) and “White and Nerdy” (Chamillionaire’s “Ridin’ Dirty”) are among his most streamed — though he’s been equally adept at literally any microgenre he takes on, from just-electrified Bob Dylan (“Bob,” entirely comprising palindromes) to arty new wave (the Devo pastiche “Dare To Be Stupid”) to crunchy Detroit garage rock (“CNR,” a tribute to Charles Nelson Reilly through the lens of The White Stripes).

“The more you listen to him, the more you get access to making [any genre of parody] sound legitimate,” says Samberg, who calls Yankovic the biggest influence on his own comedic music group, The Lonely Island. “The nature of what he does is incredibly populist. He’s not snooty about it; he’s like, ‘This is what the kids like, and as long as I have a good angle comedically, I’m going to do it.’ And because of that, it’s always appealing to young people.”

Growing up in Compton-adjacent Lynwood, Calif., Yankovic listened to rock radio, but as a teenager found playing the accordion a bit solitary. (His friends’ rock bands weren’t really interested in an accordionist joining up.) “When you take accordion lessons, I think the high-water mark is ‘Maybe someday I’ll play in an Italian restaurant or at a wedding,’ ” he says with a laugh. “I guess I was shameless. I grew up a complete nerd in high school. And when you’re not somebody that’s socially acceptable, you kind of have nothing to lose. I kind of held on to that mentality: Like, you know, ‘Who cares?’ ”

“Weird Al” Yankovic photographed April 17, 2025 at Dust Studios in Los Angeles.

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He didn’t look to any particular musician’s career trajectory as one he could follow. “It was more cautionary tales” — and one was especially haunting. One of his idols was Allan Sherman, the satirical singer best known for his 1963 summer camp send-up, “Hello Muddah Hello Fadduh!” “He was the last person to have a No. 1 comedy album before me,” Yankovic continues. “He had three No. 1 albums on, like, the pop charts — incredible! But within a few years, he completely burned out. He made some terrible choices in his personal and professional life and just went off into obscurity and sadly died a few years later. So I was always more concerned about, ‘Don’t mess it up. Keep doing what you’re doing and just try not to make bad choices.’ ”

“In a way, we’re almost always looking over our shoulders at that,” his manager Levey says. He cautiously admits that he and Yankovic have ­finally reached a level in his career where they’re “no longer at the point where every year [of continued success] is a surprise,” then adds, “I don’t actually even like saying that out loud because it sounds like you’re taking something for granted.”

But if Sherman was a rocket that blasted off only to burst into flames, Yankovic has been the opposite: one that, as Levey puts it, has kept steadily traveling through space — maybe sometimes at a slower speed than others, but never plummeting back down to Earth, buffeted by the most unexpected boosters. Like, say, Weird: The Al Yankovic Story, the 2022 parody of a music biopic that Yankovic co-wrote, starring Daniel Radcliffe in the titular role. Despite at first airing only on the Roku Channel, it won almost universal acclaim and a prime-time Emmy, while expanding Yankovic’s universe yet again.

“His longevity is a testament to his ability to be himself and stick to what his taste is, because it’s so specific,” Radcliffe says. (“Bob” is his favorite Yankovic track, and he took the opportunity on set to ask his hero how he came up with all the palindromes.) “He threads a really hard-to-thread needle between wholesome fun and something … genuinely deranged and very, very strange. And in a way that is not affected.” At a time when the culture values authenticity above all else, Yankovic is a walking example of it — never not himself.

Unwittingly proving the point, Yankovic gasps in glee as our lunch ends. “Mochi doughnuts!” He shows me a photo his wife has just texted him: a box of the treats for dessert later. Somewhat sheepishly, he explains the occasion: “Eric Idle is coming over for dinner tonight. That’s my big flex for today.”

Later that afternoon, Yankovic meets me in a park near Coldwater Canyon called Tree People. He looks a little like a more aged version of his faux-Indiana Jones in UHF: Hawaiian shirt (a Goodwill buy), sensible shoes, safari hat shielding the waning sun.

“I’m gearing up for a big tour, so I’m mostly just making sure I don’t have a heart attack onstage or pass out or something,” he says of the walks he takes in spots like this. “I think I’ve lost 20 pounds in the past couple months just because I’m not, like, eating junk food at midnight anymore.”

Yankovic’s last tour outing didn’t require much of a physical regimen. In 2022 and 2023, he took to smaller venues for The Unfortunate Return of the Ridiculously Self-Indulgent, Ill-Advised Vanity Tour, a follow-up to the first Vanity Tour in 2018. The idea, he recalls, occurred to him when “I was putting on my ‘Fat’ suit for the thousandth time and I thought, ‘Wouldn’t it just be nice to like, go out onstage and play the songs, sit on a stool and have an intimate evening with fans?’ ”

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So Yankovic eschewed the usual production level of his tours — costumes, wigs, the parody hits — for a concept, his agent Goodman says, that the musician himself wasn’t entirely convinced would work. Instead, it allowed him to visit new, smaller major-market venues (Carnegie Hall, Tennessee’s The Caverns) and ­strengthen his presence in off-the-beaten-path markets (like, say, Huntsville, Ala.) while superserving his ride-or-die fans. When the concept returned in 2022, he played 162 Vanity shows globally (extending into the next year).

“I loved it, the band loved it, the people who showed up loved it, and it definitely scratched that itch,” Yankovic says. “And now,” with the Bigger and Weirder Tour, he’s back to “doing a show for everybody.”

For Bigger and Weirder, Yankovic is in self-described “overpreparer” mode, the hyper-organized creative core of his team. “I came up with the setlist a year ago. I gave the band” — three of whom, as of our meeting, he has yet to meet — “their marching orders and said, ‘Here’s the setlist, here’s your charts, here’s the demos, here are the rehearsal days.’ ” He personally chooses and edits all the show’s video content — clips of Weird Al in Pop Culture (say, on The Simpsons or 30 Rock) over the years that will play between songs and give him and the band time for the most frantic element of the show, which the audience never sees.

“We have stage props, wigs, a lot of costume changes, and a big portion of what we need is a quick-change area behind the scenes onstage, usually 40 by 20 feet,” says Melissa King, his tour manager of nearly 20 years. On Bigger and Weirder, Yankovic will do 20 costume changes, give or take a jacket or hat; his band members will do nine; and all will occur in 45 seconds maximum.

That backstage planning ensures that in front of the audience, the man who has spent his career parodying rock and pop stars is free to embody one himself. “When I speak to [talent] buyers and say, ‘Have you seen the show?,’ if there’s a pause, for sure I know the answer is no,” Goodman says. “Because if you’ve seen the show, it’s just an immediate ‘Yeah, of course, it’s incredible.’ ”

Onstage, Yankovic isn’t just physically “working his ass off,” as Samberg says. “As a vocalist, he’s f–king incredible,” Radcliffe marvels. “He has this amazing, clear tone. His range is so impressive — he does things to his voice that, as somebody who sings a bit in musicals sometimes, if I tried that I’d hurt myself.”

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Despite the “bigger” aspects of this tour — like how it will use three trucks instead of the usual one — King is still one of just 11 people comprising the crew. “It’s very lean, but it works because we all work together,” she says. “Al’s a genuine, kind person, and because he is, that’s the way everyone in our camp is.” That ethos extends to both the fans who’ll attend (“There aren’t many arseholes who are Weird Al fans,” Radcliffe observes) and how Yankovic treats them: According to Goodman, he’s kept maximum ticket prices for Bigger and Weirder to $179.50 and has always refused to engage with platinum ticketing.

Right now, the tour is Yankovic’s focus. When he decided against renewing his Sony contract, Levey says, they tested the waters with “very limited outreach” to a mix of indie and major labels. “And we got great offers and I brought those offers to him, and he thought about it and said, ‘I’m really loving this feeling of not being under contract to anybody … Please tell these people how appreciative I am of their generous offers and we’re just not going to accept any of them.’ ”

He’s now independent in the truest sense: He has an imprint, Way Moby, that’s technically now his label, but he describes it more as existing for theoretical recording purposes. He figures he’ll put out a single here and there, contribute to soundtracks if he’s asked and, as always, remain open to what may come — like making a surprise appearance last November to duet with Will Forte on Chappell Roan’s “Hot To Go!” at a charity event or developing a Broadway Weird Al jukebox musical that he says is in the very earliest creative stages, a “bucket list” project.

“When [he had] the No. 1 album in the country, that was such a triumphant moment. I remember us celebrating,” Samberg recalls. “It just shows you — I don’t think anyone else will really touch that space. It’s his space. No one is going to say, ‘I’m going to do what Al does,’ ’cause good luck. He owns that until he doesn’t want to do it anymore.”

The world, Yankovic knows, is also not the same as when he first became famous. “I got a record deal, I got on MTV, and I kind of had the market to myself,” he reflects. “Now the playing field has been so leveled that anybody can upload their material to YouTube or various portals like that. And if the stuff is good, chances are people will eventually see it. I’d like to think that if I was coming up now, I’d still do OK, but it would just be more of a challenge.”

It’s a generous sentiment, a reminder that, as Miranda puts it, one of Yankovic’s many talents is also “reading the room.” But in its humility, it’s also a reminder that, flooded as the market may now be with funny people on the internet, none of them, still, are doing it like Weird Al: the 65-year-old who once thought he’d play accordion at weddings and Italian restaurants, who’s about to make his Madison Square Garden debut.

This story appears in the June 7, 2025, of Billboard.