Is Taylor Swift Finally Achieving Her “Hip to Be Square Moment” of Her Career?

Maybe she'll write a song about the relationship we never had

Maybe she’ll write a song about the relationship we never had

The other day, I was listening to a song on the radio, and it took me a second to realize it was one of the later Taylor Swift songs (from her 2012 album, Red), called I Knew You Were Trouble. As the song played, it started to dawn on me that I recognized it as a Taylor Swift song not because it was a great song (some of her earlier work has been phenomenal, like Enchanted) but because it had that same “I broke up with some guy and here’s another song about it” feel to it. The song wasn’t all that inspired, and for the first time, I actually found myself thinking, wow, this is the first time I’ve heard a Taylor Swift song that almost feels generically written to be a Taylor Swift song. And that immediately brought up the thought of a song I hadn’t thought about in ages, and that song is “Hip to Be Square” by Huey Lewis and the News. I guess I should sort of explain.

You see, back in 1986, on the album Fore!, Huey Lewis and the News released a song called “Hip to Be Square”. At the time, the group was riding high on its previous success with its album Sports, and it was seen as a continuation of a really strong career that was only going to be getting stronger. When this album was released, I was working for a large San Francisco convention hotel as a middle manager for the Security Department. Because this was a large convention hotel, we often received huge gatherings of hue corporations and industries, and one of them was a massive celebration of national record companies. Being a convention that catered to industry insiders, huge acts performed, and on one evening, the recently VERY successful music group Wilson Phillips was opening for Huey Lewis and the News. Because it occurred at our hotel, I was there that evening supervising Security staff who were there as the outer rim security for the whole performance. Due to circumstances of just chance, my job required me to wear a suit (not a uniform), so to anyone else there, it looked like I was probably one of the industry insiders who was probably part of the running of the show. This was made readily apparent when Chynna Phillips, their lead singer, stepped off stage after her show (and when Huey Lewis and the News was starting) and walked up to me, asking me if I could help her find a restroom. So, I escorted her to the back areas of the hotel, which was the only way to reach a location that I knew other guests wouldn’t be frequenting (which I wanted to avoid as this was basically a music star who could easily get mobbed by a crowd). Strangely enough, she took to me, and actually had a long conversation with me about music (after I stated I was a big fan of her group and felt that they were definitely on their to a great career, as it was very early in their music run), and then we got into a conversation about Huey Lewis and the News, where she stated she was in awe of their group, and for reasons I don’t even know why I shared, I indicated that Huey Lewis and his group was pretty much on its way out to the pasture. I went through a huge analysis of the song Hip to Be Square and how it was so generic that it showed their group basically lost touch with its musical roots and was either going to need to reinvent itself or never be heard from again. It was actually a really cool, long conversation, and when I brought her back to the backstage area after she finished what she needed to do, we parted in a friendly manner, and I cherished my one chance to have a conversation with someone I actually admired.

Shortly after that, Huey Lewis and the News finished their set and rushed off the stage, moving right by me. It seemed the obvious thing for everyone to say “great show” to them as they walked by, but I never forgot the look I got from the main guitarist of the group when I said it. He looked at me like I was some moron for actually complimenting him on a good show. Right then and there, I realized that it wasn’t just the song that I analyzed that was bringing about their demise; the group itself was no longer ingratiating itself towards the fans and actually looked like they were bothered by the fact that they had fans listening to their music. Not surprisingly, they fell into the “where are they now” file of musicians shortly after this industry concert.

This is kind of the feeling I’m getting with Taylor Swift right now as well. When she first made her launch into superstar ranks, there were already smirks about how all of her music is basically about how she can’t seem to hold a relationship. Hell, one of my earlier articles was a joke about how I was worried that I was going to accidentally get into a relationship with Taylor Swift and then discover she wrote about it in a song. I even imagined some of her lyrics:

You always leave the seat up

Never clean the bath tub

And always watch reruns of Star Trek.


Strangely enough, it wouldn’t be that much different from what she seems to be doing with most of her current work. I tend to believe that she has reached her “Hip to Be Square” point in her career, and like most groups that fail after this point, she either needs to reinvent herself in a way we haven’t imagined yet (kind of like Madonna did several times to continue remaining relevant), or she’s going to hit that point where people aren’t interested in going over the same sort of thing with each new album. Of course, there are always people who want nostalgia, but unfortunately, you have to put some time in the mix to make that work.

duaneIs Taylor Swift Finally Achieving Her “Hip to Be Square Moment” of Her Career?

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