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Phil Vassar Is A Poet, And If You Can’t Get Through Your Day By Listening To His Beautiful Words, You Are A Monster

Phil Vassar (Photo by Rick Diamond/Getty Images)

I have been writing this column for over a year now, and haven’t even mentioned Phil Vassar. Even worse, in three years of teaching a law school class, I haven’t unapologetically pushed Phil Vassar’s music on my students. It’s an obvious dereliction of my character traits, and I think we could all use the distraction right now of a minor, lighthearted abuse of power, in the face of all the big, dark ones sucking the air out of the room lately.

Now, about 95 percent of you are saying right now, “Who the f*ck is Phil Vassar?” Well, much like Edgar Allan Poe, or Henry David Thoreau, Phil Vassar is a literary genius underappreciated in his own time.

I was raised in a small town. I’m not ashamed of it. Sure, I got a lot of grief for, like, reading, and spending surplus time thinking. But one of the distinct advantages of growing up in flyover America was that the music in vogue there from the mid-90s to roughly 9/11 was PHENOMENAL. You might scoff at that, but all the best stuff started in obscure, backwater, low-income places. See, e.g., barbeque.

As I grew up, things changed, as they do, and many years later, I wound up as a lawyer in a (locally) prestigious firm. My good buddy at the firm, who later went on to become a commercial real estate lawyer in Biglaw, scoffed at my deeply ingrained preference for county music, saying, “Have you ever actually listened to the lyrics? It sucks; it’s just simplistic, pandering nonsense.”

Damn it, after that, I couldn’t help but listen to the lyrics. He was right. We had entered a musically superficial age. What was previously complex, gritty, risk-taking country music had largely devolved into a series of autotuned middle-America platitudes. It sucked.

Yet, Phil Vassar… oh, Phil Vassar. He’s truly an exemplar of a musically better age. When you had a feeling, he seemed to feel it. When you faced a struggle, you better believe he had struggled through the same damn thing. When you were introspective, he had a positive introspective spin for you. In his heyday, Phil Vassar wrote songs for such luminaries as Tim McGraw, Jo Dee Messina, and Kenny Chesney. But in my humble opinion, some of his finest work came when he wrote for himself.

Friday, you’re late. I guess we’ll never make our dinner date, at the restaurant. You start to cry. Baby, we’ll just improvise. Well, plan B, looks like, Domino’s Pizza in the candlelight.

That’s love, no? And real life, maybe especially for someone in the precarious relationship quagmire known as being a law student or a new lawyer?

And take exhibit B:

My next 30 years, I’m gonna watch my weight. Eat a few more salads, and not stay up so late. Drink a little lemonade, and not so many beers. Maybe I’ll remember my next 30 years.

Again, apt. One more Phil Vassar lyric, this one as originally performed by Jo Dee Messina:

Well, it’s been a long time, glad to see your face. I knew we’d meet again another time, another place. Can’t believe it’s been so many years, you better grab a chair and a couple of beers. Lookin’ good in your three-piece suit, ya’ know, I always knew you’d take the business route.

Shit, that is great. Someone understands long-term friendship.

It’s hard to say how much money Phil Vassar has made for Nashville. It’s a lot though. Moreover, he probably gets some credit for spurring certain middle-aged lawyers who came of age in the 90s into action on any given Friday afternoon.

Phil Vassar took on complexity, and sometimes hardship, but rather than being grim and defeatist about it, he was positive. His lyrics may not have been subtle, but they have always been inspiring, and relatable. So, keep an open mind. The next time you need to juice your billable hours on a late afternoon or early evening, look up Phil Vassar’s greatest hits on YouTube. What do you have to lose? And, while Phil really hit his stride for songwriting in the late 90s and early 00s, if you ever get the chance, see him live. He still performs all across the country, often for charity. You will never regret witnessing the things he does with a piano onstage. Seeing that, my friends, is a true value.


Jonathan Wolf is a litigation associate at a midsize, full-service Minnesota firm. He also teaches as an adjunct writing professor at Mitchell Hamline School of Law, has written for a wide variety of publications, and makes it both his business and his pleasure to be financially and scientifically literate. Any views he expresses are probably pure gold, but are nonetheless solely his own and should not be attributed to any organization with which he is affiliated. He wouldn’t want to share the credit anyway. He can be reached at jon_wolf@hotmail.com.