The Jets are gonna look real gay to ni-i-ight!

The year was 1985. I was a junior in high school, and our theater department (which was pretty kickin’—we did about five shows a year in two different theaters) did West Side Story.

Now, I’d grown up on my folk’s West Side Story soundtrack. (We never had the cast album until I bought it with my paper route money in junior high school.) I knew every word, every note, every fake Puerto Rican nuance of the soundtrack, though. Hell, I’d sung along and acted out every role in the show in the privacy of my sad, friendless little bedroom for the better part of a decade. So the day our theater director announced over the school PA system (with very dramatic, very gay fanfare, which I just ate up) that we were doing West Side Story as our spring musical, I … um …

Let’s just say my show of enthusiasm probably didn’t win me any macho points.

And the role I wanted more than anything? Action. The wild one. The loose cannon of the Jets. The role that would show the world that I was not, in fact, a sad, terminally bashful little homo who does victory dances in AP History class when he hears the theater department is doing his favorite musical. I didn’t care as much about playing the role, though, as I did about singing “Gee, Officer Krupke!” It’s a totally cool song, and it starts on that hard-to-hear tritone that I was certain I was the only male in the whole theater department who could be relied on to hit it right on the money night after night. I knew the song cold—tritone and all—which meant the role was rightfully mine.

Unfortunately, my audition was too much tritone and not enough loose cannon. And Joel, a hunky little straight guy who had the presence of mind to actually act at the audition, got the part. And I was crushed. Truly, deeply crushed.

But I persevered through rehearsals in my role as Third Jet From The Left, and I got a couple featured dance roles (tritones and battements dégagés—is there no end to my homosexuality talents?) and I let myself revel in all the magic that came along with Actually Being In West Side Story.

And on opening night, when Joel (who was quite awesome in the part) went to sing my his big solo … he forgot the words. And I hung there (the set was all about scaffolding), three Jets in from the left, staring dumbfounded as he stumbled through his first verse. And I was filled with a weird mix of horror and pity and self-righteous indignation and even a little bit of Schadenfreude.

But that’s not actually the point of this post. The point is that I went through some old photo albums last weekend and I found a mountain of embarrassing pictures. And trust me: When you’re an awkward little homo in Iowa in the ’80s, every picture you take is pretty embarrassing.

But I’m 37 now and I can look back and laugh. On the outside. And I’ve been sneaking over to our scanning station at work whenever I could spare a few minutes the last few days, so my blog is going to be a very painful walk down memory lane over the next few weeks.

Here is the only picture I found from West Side Story. And man, there’s nothing sadder than a middle-class white gay boy pretending to be all butch and shit like he’s down with the PR kids, yo.

That’s my dad’s jean jacket, which was way too big. But I rolled up the sleeves. To the elbow. Just like they do in the gangs. And if you look closely, you can see the moussed-up nightmare of waves and curls I somehow decided gave my hair 1950s New York street cred. And then there’s that smirk. That I-live-a-very-comfortable-life-in-a-town-with-great-schools-so-you-better-run-sucka smirk. The whole effect is pretty scary, but not in the way I intended.

That’s Beth next to me. I was always impressed with her acting, though I think she was little more than Third Jet Girl From The Left in our show. (The next year, she and I played the leads in Oedipus Rex. Which was far more exciting than starring in some stupid old blockbuster dance musical.) Beth told me at our 10-year reunion that she was in med school, so maybe she can surgically remove the last of my embarrassment if I see her at our 20-year this year.

Stay tuned for more of Jake’s A Dork And I Have The Pictures To Prove It!

Next up: my horrifying experiment in gymnastics leotards.