The Big Squeeze: Day Seventy-Five: "Airline Amy" from Off the Deep End

The Big Squeeze is a chronological trip back through the music of “Weird Al” Yankovic. The column was conceived with two big objectives in mind. First and foremost, I want to inspire conversation and appreciation of a true American hero. Even more importantly, I want to promote the Ridiculously Self-Indulgent, Ill-Advised Vanity edition of the Weird Accordion to Al book, which is like this column but way, way, better and this column is pretty damn good, because it has illustrations and copy-editing and over 27 new illustrations from Felipe Sobreiro and over 120 new pages covering The Compleat Al, UHF, The Weird Al Show, the fifth season of Comedy Bang! Bang! and the 2018 tour that gave the extended version of the book its name. 

Author’s Commentary: The nice thing about this column is that it gives me an opportunity to write about things I did not catch the first time around. Or the second time around. Or the third. What I’m saying is that at this point I have spent a LOT of time with these songs, and these write-ups.  

Yet I’m still catching new things all the time. That’s a tribute to the depth and richness of Al’s catalog or my sloppiness or quite possibly a combination of the two. 

For example, in the below entry I never mention that “Airline Amy” is a pastiche less of an artist than a specific song. In this case that song is Nick Lowe’s “Switchboard Susan”, which has a premise so similar to that of “Airline Amy” that I think of it as an alternative version as much as a style parody. 

“Airline Amy” and “Switchboard Susan” are ironic, satirical, alliterative love songs about deluded men trying to turn their professional relationship with the titular working girls into something romantic. 

In “Airline Amy” the object of desire is of course the eponymous waitress in the sky while in “Switchboard Susan” the myopic singer pines long-distance for a telephone operator. 

Truth be told I prefer “Airline Amy” to Lowe’s loopy love song. As with parodies like “Word Crimes”, Al didn’t just build on his inspiration: he improved on it as well. 

The original Weird Accordion to Al article: 

On Off the Deep End, Al’s originals aren’t just clearly preferable to every parody other than “Smells Like Nirvana.” They’re also far more sophisticated, both lyrically and musically. Then again, considering that the album finds Al spoofing the low-wattage likes of MC Hammer, Gerardo, New Kids on the Block and Milli Vanilli, in addition to Nirvana, that’s not exactly high praise. 

But Al’s sublime originals do merit high praise. “Airline Amy” is a typically terrific Al original but it’s an anomaly in other ways. Musically and lyrically, it’s surprisingly subtle and understated, with a refreshing power pop vibe complete with chiming, Byrds-by-way-of-R.E.M guitar and smart, quirky lyrics. 

I’ve written extensively about the lousy Lothsarios in Al’s oeuvre and how his would-be womanizers often mistake their own mental illness for love. That’s true of the singer of “Airline Amy” as well but where Al’s cracked romantics frequently seem to pose both a danger to themselves and the women unlucky enough to end up their objects of desire, not to mention the world at large, the singer of “Airline Amy” seems fundamentally harmless, if also hopelessly deluded. 

The song is sung by a true romantic who mistakes the titular waitress in the sky’s devotion to her job for romantic attraction. It’s a decidedly one-sided love affair. “Every one of our dates is at thirty thousand feet” the singer boasts without realizing that what he sees as the exquisite dance of l’amour fou is actually more a matter of a professional doing their job. 

When the titular stewardess points out the exits, refills his coffee, gets him headphones and demonstrates how to use an oxygen mask in case of emergency, our adorably misguided singer is convinced she’s flirting up a storm, engaging in a little high-altitude foreplay. “Airline Amy” is agreeably deadpan: it sure sounds and feels like an infectious, upbeat power-pop love song. You have to really listen to the lyrics to get the song’s comic conceit, and even then it’s abstract and more than a little conceptual.

“Airline Amy” is strong enough that it doesn’t really need to be a comedy song, or even particularly funny. It would be a winner even without the comic hook of a deluded frequent flyer mistaking professionalism for affection and proximity for an actual relationship. If “Airline Amy” was just a catchy power pop love song about a pathologically optimistic and hopeful young man in love with a stewardess it would still be a good song, but it would not be a “Weird Al” Yankovic song. 

Like “You Don’t Love Me Anymore”, with its rhyme about losing a little bit of self-esteem “that time that you made it with the whole hockey team”, “Airline Amy” contains one of Al’s most ribald-sounding lyrics in the singer’s vow to get the object of his deluded affection in an “upright locked position.” I’m not even sure what that means, but it sure sounds dirty yet incongruously innocent at the same time, not unlike the song itself. 

The strange, deluded men of Al’s warped love songs comically misunderstand both the emotions of the people they’re in love with, and the way love and the world work. Oftentimes that has an aggressive, sinister element but that’s not the case here. The singer is a fool, all right, and a low-key lunatic but he’s also truly lovestruck, albeit misguided. 

If “Airline Amy” isn’t hilarious, that’s at least partially by design. Al isn’t going for big laughs here, so much as he is knowing chuckles. “Airline Amy” doesn’t reach the comic heights of some of Al’s other work but little in his catalog can match it for sunny charm and warped innocence. 

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Also, BUY the RIDICULOUSLY SELF-INDULGENT, ILL-ADVISED VANITY EDITION of  THE WEIRD ACCORDION TO AL, the Happy Place’s first book. This 500 page extended edition features an introduction from Al himself (who I co-wrote 2012’s Weird Al: The Book with), who also copy-edited and fact-checked, as well as over 80 illustrations from Felipe Sobreiro on entries covering every facet of Al’s career, including his complete discography, The Compleat Al, UHF, the 2018 tour that gives the book its subtitle and EVERY episode of The Weird Al Show and Al’s season as the band-leader on Comedy Bang! Bang! 

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