The Triumph of Weird Al

Inside the parody king's amazing comeback - and why he's ending his career as we know it

Weird Al Yankovic at home in Los Angeles with his poodle, Sandy in July 2014. Credit: Chris McPherson for Rolling Stone

'Weird Al" Yankovic needs a moment to himself. It's a beautiful Saturday morning at his sprawling house in the West Hollywood Hills, and he's just gotten news he can barely process: His newest album, Mandatory Fun, is about to enter the charts at Number One. It's an amazing feat: No comedy LP has topped the charts since the last months of the Kennedy administration (when Allan Sherman did it with My Son, the Nut). Tears well in Al's eyes. "Sweetie," says his wife, Suzanne, "it's people loving you like they always have. It's OK to cry."

Al walks into his bedroom to be alone. "I thought that was never, ever, ever going to happen," he says later. "I figured as a culture we don't put comedy albums at Number One anymore."

The news is the culmination of an insane week for Al, 54. In mid-July, the parody guru released eight new videos in eight days – spoofing everything from Lorde's "Royals" ("Foil") to Iggy Azalea's "Fancy" ("Handy") to Robin Thicke's "Blurred Lines" ("Word Crimes"). His record label wouldn't properly bankroll the videos, forcing Al to cut deals with Web outlets like Funny or Die and College Humor.

The clips racked up an average of nearly 4 million views apiece and set off an explosion of Weird Al mania, the likes of which hadn't been seen since his Michael Jackson parody "Fat" was in regular rotation on MTV back in 1988. Al's name trended on Twitter throughout the week, right next to Vladimir Putin and LeBron James. Mandatory Fun sold 104,000 copies during the week. "Word Crimes" rose to Number 39 on the singles chart, making Al one of only three artists to have a Top 40 hit every decade since the 1980s (the other two: Michael Jackson and Madonna). "This is a tipping point for him," says his longtime manager, Jay Levey.

All the love was validation for an artist whose appeal now spans two or three generations. "When I started doing this, a lot of my fan mail came from 12-year-old boys," says Al. "But my audience has grown enormously. Those 12-year-old boys grew up and got their own families."

"'Eat It' on 45 was the first record we ever owned," says Akiva Schaffer of the comedy-rap trio the Lonely Island. "In the lyrics he makes every line a joke, which is something we aspire to." Seth Meyers recently gave Al a heartfelt tribute on his late-night show. "I remember the first time I heard 'Eat It' on the radio," Meyers said. "I was so excited I asked my dad to pull the car over. I couldn't believe we lived in a world where someone could take a song you knew, change all the words and make it funnier."

When Al began work on Mandatory Fun last year he sought permission as he usually does, from every artist he planned to parody. (Technically he doesn't need to but he does it to avoid potential conflict with his targets.) Al has struck out a few times in the past with James Blunt and Eminem among others. This time around he got a yes from everyone - except at first Iggy Azalea.

When Al got only radio silence from Azalea's camp he decided to take drastic measures. "I was like, 'Wherever Iggy is, I'm flying out to talk to her,'" he says. "She was playing in Denver, so I flew out there the day before I was going to record the song."

Al arranged with the promoter to wait for Azalea backstage. "I'm not 100 percent sure she even knew who I was," he says. "But I didn't want to preface the conversation with, 'Do you know who I am?'" Azalea scanned the lyrics to "Handy" and quickly gave her approval. Al immediately flew back to Los Angeles and wrapped up work on the song, about a supremely confident fix-it guy ("Maybe I'll just rewire your house for fun/I got 99 problems, but a switch ain't one").

Al writes many of his parodies in his home's large music room, which features a Kurzweil keyboard, a mini drum kit and a MacBook. A song can take months of editing to get right. He pulls up a draft of "Handy" on his laptop. In the finished version of the song he went with "Call me I'll come rushing over with my bag of tricks," but he also considered "Call me, I'll be in the office daily from nine to six," and an array of other alternate lyrics. "There are several stages that go before this," he says. "There's a lot of different ways you can phrase things."

Down the stairs from Al's home studio sits a tiny closet that doubles as a Weird Al museum: It contains at least 400 Hawaiian shirts the patchwork pants he wore on the Tom Snyder-hosted Tomorrow show in 1981 and boxes of carefully organized mementos.

One secret to Al's success is that, under his goofy exterior, he's got a formidable intellect. In one box rests songs he carefully transcribed for the accordion when he was in elementary school, and a program from the 1976 commencement ceremony for Lynwood High School, where Al was the valedictorian. He gave a speech titled "The Future: Its Price," in which Al horrified the crowd by warning that the melting ice caps doomed everyone on the planet.

Another secret to Al's success: Suzanne, a former senior vice president at 20th Century Fox. She helped modernize Al's look a few years ago by urging him to ditch his signature Hawaiian shirt. The couple have been married for 14 years, and their affection for each other is still obvious: She calls him "sweetie love" and he calls her "honey."

Nina, the couple's 11-year-old daughter, clearly inherited her father's smarts, though she doesn't share his obsession with pop culture. She has little interest in owning a cellphone, spending time on the Internet or even watching TV. Today, she is perched on a bean-bag chair, reading Animals of the Little Wood, an out-of-print 1967 children's book about forest creatures. "She's such an ideal kid and really has the best qualities of me and my wife," says Al. "Where did we go right?"

A few months ago, Al made a major decision: Mandatory Fun will be his last studio album. It fulfills a 14-record deal he began with Warner Bros. back in 1982. More important, Al feels his new songs could have been even bigger, had he not been stuck under contract. For instance, he wrote his Robin Thicke parody a year ago and wished he could have released it when "Blurred Lines" was peaking in popularity. But the label refused to let him put it out until the entire album was ready. "It irks me because there's obviously a gazillion parodies of that song on YouTube," he says. "I realize I'll never be the first person to parody any given pop song but I don't want to be the millionth."

Now he just wants to release singles or EPs on the Web. That way they'll get out while the songs they're parodying are still on the charts. Will it work? "I've been counted out more times than I can remember," Al says. "I just like to prove people wrong."