How “Weird Al” Yankovic pranked his dates

Thinking about “Weird Al” Yankovic as a man-about-town bachelor type is almost as funny as his musical persona. While he’s happily married with a child nowadays, during the height of Yankovic’s initial fame in the late 1980s and early 1990s, Yankovic was single and ready to mingle. If you were a lucky lady in Los Angeles around that time, chances are you could have scored a date with “Weird Al”.

That time has come and gone, but Yankovic did share some hilarious insights into his dating life while being interviewed by Lary Wallace in 2014 for The Paris Review. While parsing through the various appearances throughout pop culture that Yankovic has done over the years, the question comes as to what Yankovic’s first cameo was. 

“The first time he ever did a cameo was The Naked Gun (1988),” Wallace writes. “Al was single then, and he took a series of first dates to the movie, not telling any of them he was in the film. When he’d show up on screen emerging from that airplane, ‘they just flipped out‘, he told me, especially when they realized he was wearing that exact same Hawaiian shirt, in two totally different realms yet at exactly the same time.”

A few things to think about: first off, Yankovic was pulling off multiple first dates in those days. If you ever think you’re a loser because you can’t land a date, just remember that “Weird Al” was able to get “a series” of women to go on dates with him. It’s not like Yankovic isn’t good-looking; he’s just… striking, especially when he had his “glasses and perm” combo in the late 1980s.

Secondly, not only is Yankovic getting a bunch of first dates, but he went on them wearing a Hawaiian shirt. It’s the single most “Weird Al” Yankovic thing that I’ve ever heard in my entire life. I’m sure the reactions were worth it, but it’s also not surprising to hear that this exercise required a couple of different first dates. That’s a difficult thing to top on the second dinner. Maybe if Liam Neeson ever gets his Naked Gun reboot off the ground, Yankovic and his Hawaiian shirt will make a return.

Check out Yankovic’s cameo in The Naked Gun down below.

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