#116, “A Pirate Looks at Forty,” Jimmy Buffett (1974)

150 Favorite Songs: #116, “A Pirate Looks at Forty,” Jimmy Buffett (1974)

My parents had pretty different tastes in music. A few years ago, when I spent a lot of time driving between Austin and Los Angeles, I asked my friends on Facebook for hour-long playlists of their favorite songs to keep me company on the road. (This was a really good idea, incidentally—I got a couple dozen lists, and I still listen to some of them today. It’s a fun way to get to know people!) My dad’s playlist was a mix of soul, jazz, and ‘60s and ‘70s FM rock radio—Otis Redding, Ray Charles, Miles Davis, Herbie Mann, John Mayall, Bob Dylan, Santana, Neil Young, Dusty Springfield, stuff like that. My mom’s was more mellow—Billy Joel, Bread, Simon & Garfunkel, Gordon Lightfoot, Cat Stevens, that sort of thing, plus a good assortment of more recent country songs. (Both of them had a Beach Boys song, though my mom went with “Surfer Girl” and my dad had “Good Vibrations.”) And, of course, my mom’s had Jimmy Buffett, because her dedication to Jimmy Buffett means that his music has been a part of my life for as long as I can remember.

I have affection for the kind of music both of my parents like, I tend, as a rule, to gravitate more towards the stuff my dad listened to than what my mom does. As I’ve gotten older, though, I’ve realized that while I listen to more of the sort of thing my dad liked, the way I appreciate music has a lot in common with my mom. She makes friends with her records in a way that I do—if there’s something she likes, she spends a lot of time with it, plays it over and over. (I have a distinct memory of her having made a mix tape when I was a kid that had “We Didn’t Start the Fire” several times on the same side!) She’s sought out new music at points in life when most adults are content to listen to whatever they grew up with; in her forties, having grown tired of oldies stations, she decided to start listening to country radio, and get into an entire new genre of music, which I always thought was a very cool thing to do. And she’s incredibly devoted to her favorites. Up until Jimmy Buffett’s death last year, I could ask what she was doing on any given Saturday night, and she would often be watching a livestream from wherever Jimmy Buffett was playing.

So I’ve grown up wth Jimmy Buffett’s music—but I also have complicated feelings toward it, because there are really two Jimmy Buffetts, and I have a lot more time for the one he was not particularly interested in being. The first is an introspective songwriter who wrote about the feeling of being in the wrong place, wrong time, watching life go by and not sure what to do about it—the stuff a lot of my favorite songs get into. The second is the one you probably think of when you hear his name—a Hawaiian shirt, a keg of beer, a lot of happy people screaming back “salt! salt! salt!” while the big cornball played “Margaritaville.” There’s nothing wrong with playing songs in a way that an arena full of people like to create chant-along parts to, of course, but you’ve been with me here for almost forty songs now and you know that is not the first thing I look for in music.

(“Margaritaville,” for example, is a song that actually does speak to me, in some ways, but then turns me off in others. Despite its island trappings, it was actually written in and about Austin, where I’ve lived for many of the past twenty years. He wrote the song at a strip mall Mexican restaurant on Anderson Lane in 1976, roughly where the San Francisco Bakery & Cafe is now, though no one is sure exactly where—somehow, there’s not a statue commemorating the event! On the surface, it’s not far off from the sort of thing that, say, Townes Van Zandt wrote—a song about wasting your life and feeling stuck. But while Van Zandt clearly felt immense despair at that prospect, Jimmy Buffett was rather more sanguine about it—it’s his own damn fault, but what can you do about it? Eventually, the song became a hit and he made a billion dollars and made my mom and many other Parrotheads very happy. This is a good thing, but all of that context just means that I can’t hear it the way I’d like to!)

Anyway, let me dig my way out of those parentheses and back to the point, which is not “Margaritaville,” it’s “A Pirate Looks at Forty. ” This is a song I love because it has a lot of that same introspection, but it doesn’t have all the corny weight behind it. It’s more wistful—slide guitar instead of recorders and flutes, minor key instead of major key, with a lullaby quality to the way Buffett sings to “mother mother ocean,” a narrative of juvenile daydreams that leave the narrator in a state of arrested development that he recognizes, but can’t imagine how to break. He sings, “I go for younger women / lived with several a while,” then turns to devastating lines about how they leave until he charms them back for a little while, a pattern that obviously doesn’t do him or anyone else any good, but which he accepts is pretty much all he’s got. When it reaches the song’s conclusion, it isn’t really a conclusion at all—it’s just the last thing he sings before the song ends. “I feel like I’ve drowned / gonna head uptown,” repeated twice, before the narrator goes to a bar and gets drunk and then, presumably, wakes up in a sweat at four A.M. praying once more to Mother Mother Ocean as he accepts that he’s looking at forty and the only thing that’ll be left for him after he’s off the water is to once more head uptown. Repeat, repeat, repeat.

“A Pirate Looks at Forty” is a hit, part of the Jimmy Buffett canon—it’s not some obscure b-side I dug out of a closet somewhere—but he doesn’t have many songs quite like it, that hit the same melancholy notes without getting cheesed up the way that so many of his songs did. He played it pretty much every night, but usually as the closing song of the set, one that the crowd who wanted to sing along had to join with on the song’s own terms, while he strummed it out gently. “Margaritaville” is a song, but it’s also a chain restaurant, a casino, a cruise ship, and a retirement community; “A Pirate Looks at Forty” is just a ballad, and I wonder sometimes how many songs like it Jimmy Buffett might have written if he hadn’t instead come up with a surprise hit four miles from my house, years before I was born, that I’ve heard so many times that it sounds like white noise. I’m glad for him, and my mom and all the other Parrotheads, that he became the Jimmy Buffett that he did. But when I listen to “A Pirate Looks at Forty,” I still wish I’d gotten to hear the songs he might have written if his life had turned out a little more like that of the song’s narrator.