“Weird Al” Yankovic didn't intend to play Los Angeles this year. His last hometown gig was less than a year ago, at the Greek Theatre in September 2015. But an amazing opportunity came his way: The Hollywood Bowl wanted the famed parodist to headline the historic venue, accompanied by a full orchestra.

“That's not really the kind of thing you can say no to,” Yankovic says by phone.

On July 22 and 23, the singer of comedy-pop hits like “Eat It” and “White and Nerdy” will headline the Bowl for the first time. It's a momentous occasion, but it's not actually his first appearance under the famed bandshell. In 2014, Yankovic joined an evening called “The Simpsons Take the Bowl” to perform “Homer and Marge,” a tribute to the animated couple sung to the tune of “Jack and Diane.”

It was that performance that brought Yankovic to the attention of the Hollywood Bowl's programmers. “It sort of blew everybody away and reminded us that this guy is an amazing performer,” says Johanna Rees, the Bowl's associate director of presentations.

Not long before the Simpsons gig, Yankovic released Mandatory Fun, his 14th studio album and the first comedy LP in more than 50 years to hit No. 1. “It was sort of this serendipitous moment. Our eyes were opened,” Rees says.

It helps, she adds, that Yankovic's shows are family-friendly, which is great for a venue that attracts concertgoers of all ages. In fact, Yankovic, who grew up in Lynwood, was about 6 years old when he first made the trek to the Bowl by bus with his mother. He doesn't recall the names of the performers that night, just that it was a classical music event and it was “an amazing experience.” He adds, “It was literally half a century ago.”

When Yankovic says “literally,” you know he's not using it as a substitute for “figuratively.” The 56-year-old parody master addressed that misuse of English in “Word Crimes,” a grammar-intensive riff on Robin Thicke's “Blurred Lines,” from Mandatory Fun. Poor grammar is a pet peeve of Yankovic's; he's been known to copy-edit his own press releases.

As a songwriter, Yankovic is a list-maker, whittling down ideas into comedy gold. His style may seem easy to mimic — and certainly a good chunk of would-be YouTube stars have tried to do so — but there's a precision to his work that can't be matched. He's often squeezing new, unexpected stories into pre-existing templates and making them fit perfectly.

“Even though what I do is ostensibly silly, there's a lot of effort and crafting [that] goes into it,” he says. “I just want to make sure that everything that I put out is as good as it can possibly be.”

Yankovic attended his first Bowl show “literally half a century ago.”

It wasn't always this way. When he was starting out, “I would basically write down the first thing that came to my mind and record it because I thought that it had a very short shelf life,” he says. “I was basically writing songs just so I could get it played once on the Dr. Demento show. Nowadays, when I write something, I realize that there are people that actually care about what I do.”

This year marks the 40th anniversary of Yankovic's debut on Dr. Demento's legendary comedy and novelty radio show. A bright, nerdy kid who started college at 16 and hung out in the comedy section of record stores, Yankovic also was an accordion player, who recorded quick ditties on a cassette recorder.

“I had minimal skill and talent, but I think I just had a lot of unearned confidence,” he says. “I was pretty shameless.”

Still, that shamelessness paid off. He graduated college with a single already under his belt: “My Bologna,” a parody of The Knack's “My Sharona.” It changed the course of his life.

“I thought I would be an adult and have a respectable job at this point in my life,” he says. “It just hasn't worked out that way.”

Through the years, Yankovic has been a pop culture mainstay, taking on the biggest hits of the day with a keen and often timeless sense of humor. In the '80s, he adapted the songs of pop stars like Madonna and Michael Jackson to fit his oddball wit. In the '90s, he tackled grunge with “Smells Like Nirvana” and hip-hop with “Amish Paradise.”

More than 20 years into his career, just when it seemed that his shtick might be wearing thin, Yankovic scored one of his biggest hits with 2006's “White and Nerdy.” The parody of Chamillionaire's rap song “Ridin'” hit big — thanks, in Yankovic's view, to unintentional good timing, as the song became an anthem for the new wave of nerd culture.

“All of a sudden, people were trying to show that they had nerd cred, which is certainly nothing that happened when I was in high school,” Yankovic says. “A nerd was not something you aspired to be when I was a teenager.”

Since “White and Nerdy,” Yankovic has stayed at a creative peak. In some instances, he's lampooning more than popular songs; he's also tapping into the current cultural climate. “I'm not trying to achieve any kind of social change, although sometimes I'll touch on topics that may be considered socially relevant or political. But that's never really my main ideal,” he says.

In the midst of an era where jokey viral hits come and go as quickly as the flu, Yankovic is still cranking out humorous jams that have a bit of longevity. Mandatory Fun is now 2 years old. The songs that he parodies on the album, like “Blurred Lines,” “Fancy” or “Royals,” are practically oldies by internet standards. But the ideas that he injects into them remain on point. “Royals” may no longer be on your radar, but Weird Al's version, “Foil,” is still all too relevant, thanks to its lyrics about tinfoil hat–wearing conspiracy theorists.

Where once Yankovic was the parody guy, now there are lots of people churning out spoofs online. “I'm not the only game in town anymore,” he says. “I think that it's healthy that the playing field has been leveled, and it just makes me step up my game a bit more. It is a challenge, but it's something that I look forward to.”

Right now, Yankovic's biggest challenge is his two-night engagement at the Bowl. In another “Weird Al” first, he'll be accompanied by a full orchestra. He has been working with arranger Sean O'Loughlin on merging songs like “Smells Like Nirvana,” “Fat” and even one of his trademark polka medleys with the sounds of the Hollywood Bowl Orchestra.

The process didn't involve much on Yankovic's end. After one lengthy meeting at his home with O'Loughlin, the arranger went off and produced MP3s laying out the orchestral parts. They haven't even rehearsed together yet. That won't happen until the afternoon before the first performance. “It's a little bit scary for me,” Yankovic admits, although he adds that he's certain everything will turn out fine.

The shows will mark another high point for someone whose career has lately had a lot of them. Beyond the hit records and tours, Yankovic has also had some success in the TV realm. He recently joined the fifth season of Scott Aukerman's IFC series, Comedy Bang! Bang!, as the show's bandleader. But his music is still Yankovic's calling card.

“It's really ironic, because the kind of music that I do, nobody thought I would have a career to begin with,” Yankovic says. “Meanwhile, I'm still kind of hanging on.”

WEIRD AL TAKES THE BOWL | Hollywood Bowl, 2301 N. Highland Ave., Hollywood | Fri.-Sat., July 22-23 | $14-$125 | hollywoodbowl.com

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