Cities are great! Who doesn’t love a good ole city? But, then again, there are so many cities in our big, wide world. How can anyone possibly decide which to prioritize visiting, and more importantly, which to avoid like the plague? At Paste, we are, somewhat notoriously, big fans of music. As such, we couldn’t think of a better way to answer the age-old question of “Which city sucks the hardest?” than by examining every single song that has ever been written about a city then compiling a list that spans the entire spectrum of opinion, from the very best titular city to the absolute worst.
In this list, we will be taking each song’s description of their titular city as gospel, and will be analyzing said city’s worth strictly on those terms. The sole requirement for the songs on this list is that they must have a city in the title, and only a city in the title (exceptions have been made, of course, where we see fit). This decision was made to narrow down the field of possible selections, because there are many, many songs about cities and, as a result, it would be very difficult to create a comprehensive ranking of every city-titled song in the entire history of music. But while this list may not be comprehensive—as that would be virtually impossible—it is thorough. Christmas is coming up, and whether you’re looking for a winter vacation spot or a brand new home, we’ve got you covered.
Based on this (and nothing else), I kind of think living in Melbourne would fix all of us, actually. Who doesn’t want to start over? Who doesn’t want to forget their mistakes? Who doesn’t want to remember their dreams? Melbourne, you should officially top everyone’s bucket list. (Also, on a related note, if there was a tourist boom in 2018, Melbourne officials should consider sending Jeff Rosenstock a gift basket.)
Talk about a positive take on San Fran! According to McKenzie, it’s love and gentleness and summertime and flowers all the way down. The only negative I can think of is that some people might be allergic to pollen, and it sounds like there are a lot of flowers being worn there constantly, so you might need to invest in some tissues were you to ever spend an extended period of time there. But honestly, that is a low, low price to pay for everything it sounds like San Francisco has to offer, so I wouldn’t let a sneeze or two stop you from venturing on the California vacation of your dreams.
It sounds like Mykonos is essentially Melbourne, but with a tad more uncertainty. Fleet Foxes seem to be a little more hesitant than Jeff Rosenstock to slather such universal praise on their chosen “M”-initialed city, choosing to instead hedge their bets with a “maybe:” the sun in Mykonos will “maybe dissipate / shadows of the mess you made.” That’s still pretty great, obviously, but why go to a place that will maybe erase your mistakes instead of one that undoubtedly will? There are a couple reasons, actually: maybe there are no flights available to Melbourne, or maybe tickets are way cheaper to Mykonos. As such, Mykonos seems to be something of a budget Melbourne; it’s great, but you should probably go to Melbourne instead—unless, of course, you’re facing some sort of extenuating circumstances that make Mykonos the better option.
While some of this track’s enjoyment of Asheville seems tied to a specific person the speaker vacationed there with, this song, unlike some others on this list, does actually provide plenty of helpful information about the North Carolina city regardless of one’s relationship status. According to Theo Zumm, Asheville has great graffiti, a night air alit with cool breezes and even makes you recognize the beauty in things often taken for granted. All in all, Asheville is apparently such a great vacation spot that the song ends with the speaker declaring that, despite still being strangers (relatively), the pair should take another trip together soon, concluding that “I don’t know you all that well, but I’d like to.” So if you’re looking for a place to visit with a new friend or a new partner in the hopes of solidifying your relationship with them, Asheville sounds like a perfect choice.
This is an extremely helpful song to consult when planning a vacation, because it gives you insight into two cities at once: Do not book a trip to Constantinople, because it no longer exists; however, feel free to book a trip to Istanbul (especially if you were originally hoping to check out Constantinople), because it is the new Constantinople. Besides, Turkish delights sound nice, as do moonlit nights. I would say it would be difficult to live there because you might keep calling it Constantinople by accident, but They Might Be Giants already thought of that and created this nifty song to help you remember. Thanks, guys! Sounds like a delightful, illustrious, mysterious, moonlit place. Put it on your list!
20. Conor Oberst and the Mystic Valley Band: “Sausalito”
“We should move to Sausalito / Living’s easy on a house boat / Let the ocean rock us back and forth to sleep / In the morning with the sunrise / Look in the water see the blue sky / As if heaven has been laid there at our feet”
The speaker of the song fantasizes about moving to Sausalito, where the sunrise on the water is so beautiful that it feels like “Heaven has been laid there at our feet.” But while living on a houseboat sounds idyllic, there’s a decent chance that, in reality, you might get seasick after a while, so I’m not sure how sustainable that lifestyle is long-term. I guess it depends on the person, really, and how likely they are to get seasick. Honestly, I think I’d be fine, but I do know my mom gets seasick sometimes, and I wouldn’t want her to avoid visiting me or anything. But if that’s not a concern for you (or if you do want your mom to avoid visiting), perhaps consider moving to Sausalito!
19. Phoebe Bridgers: “Kyoto” (+ “Kyoto” by Yung Lean)
“Day off in Kyoto / Got bored at the temple / Looked around at the 7-Eleven / The band took the speed train / Went to the arcade … / Dreaming through Tokyo skies / I wanted to see the world / Then I flew over the ocean / And I changed my mind”
According to Phoebe Bridgers, Kyoto has some pretty cool sights: a temple, a 7-Eleven, a speed train, an arcade, a Goodwill, chemtrails and even old-timey payphones! However, despite all these fun tourist attractions, Bridgers seems less than fond of the city: “I wanted to see the world / Then I flew over the ocean / And I changed my mind.” What’s so bad about Kyoto that it single-handedly changed her mind about the joys of traveling? Frankly, I’d be lying if I said I wasn’t curious. I know this is going against Bridgers’s advice, but if you’re anything like me, you might feel inclined to check out those payphones and arcades and, primarily, figure out what the hell Kyoto’s deal is.
If that’s the case, I assure you that your curiosity will only be compounded by Yung Lean’s take on the city. I looked to his “Kyoto” in the hopes of finding some answers as to what it is about the Japanese city that could make Bridgers regret even the concept of seeing the world, but aggravatingly, I found literally nothing of use. Perhaps Mr. Lean forgot the song was about Kyoto? He talks about Europe (where he and the Sad Boys sip crystal), he talks about Narashino (where he sees his own white shadow), but bafflingly, he does not provide even a smidgen of information about his titular city. I admit, this makes me more intrigued than ever before. Kyoto is an enigma; I must understand it. If you find yourself in the same boat, hit me up; We’ll book a joint trip and figure it out together.
18. Neil Young: “Philadelphia”
“City of brotherly love / Place I call home…. / Philadelphia / City of brotherly love / Brotherly love / Sometimes I think that I know / What love’s all about / And when I see the light / I know I’ll be all right / Philadelphia”
Neil Young does make Philadelphia sound pretty great, but I gotta say, he doesn’t seem to know that much about it. I’ve only been to Philly once, so if you told me to write a song about the city without being allowed to look up anything about it first, I kind of feel like the song I’d end up with would be pretty similar to this one, in that there would be no real information given about Philly (because I don’t really know anything about it), and I’d just end up awkwardly repeating the one thing I do know—that Philadelphia is known as the “City of Brotherly Love”—a lot of times, and basing the song around that. So while it’s true that Neil Young has only good things to say about Philly, I’m just not entirely convinced he’s much of an authority on the city? As such, I must advise you to take his praise with a grain of salt.
17. Silver Jews: “New Orleans”
“There is a house in New Orleans / Not the one you’ve heard about, I’m talking about another house”
Think of a song about a house in New Orleans. Think of one right now. What song are you thinking of? Don’t lie, it’s the “House of the Rising Sun.” But this song about a house in New Orleans, however, is much better—not even just subjectively, at that; it is quantifiably better. In “New Orleans,” David Berman mentions two houses in comparison to the Animals’ one, and two is mathematically greater than one, so algebraically, this song is objectively superior. Further, Berman alerts listeners to the little-known fact that there is, in fact, more than one house in New Orleans, which is really quite heartening. So if you like cities with multiple houses, New Orleans might be the city for you. Additionally, there appears to be gold left by Spanish gentlemen inside of cellars in the (multiple!!!) houses in New Orleans, so it’s a great place for treasure hunting, especially if you have a grudge against Spanish gentlemen.
Unfortunately, not all is as it seems in New Orleans, as “there’s trouble in the hall,” up the stairs, in the air, and “trouble in the trouble” itself, which sounds a little concerning. In any case, as someone who likes houses and gold but is not a fan of trouble, I feel pretty mixed on New Orleans, but I appreciate David Berman for his very comprehensive overview. As such, I advise weighing your personal preferences for houses/gold against your hesitation toward trouble, and going from there; the conclusion reached will likely vary between different people.
16. Sufjan Stevens: “Chicago”
“I fell in love again / All things go, all things go / Drove to Chicago / All things know, all things know”
To be frank, as great as this song is, it is not very helpful when it comes to aiding listeners in discerning whether or not they should visit Chicago. All it really tells us is that the speaker fell in love again, which apparently caused them to drive to Chicago, and then they sold their clothes to the state, and they also made a lot of mistakes. To make matters worse, it’s a little unclear where in the timeline the mistakes were made. Was it in Chicago? If so, maybe avoid the city so as not to make mistakes. Or was it before Chicago, and Chicago is where the speaker went after the mistakes, and where they matured enough to recognize those aforementioned mistakes? If so, Chicago sounds like a great place for personal growth! Do you see the issue here?
There are a lot of confusing refrains in the song as well: all things go, all things grow, all things know, and so on. “All things go” feels sad, because many of us don’t like loss, so if all things in Chicago go away, perhaps you should not go there. At the same time, though, “all things grow” sounds hopeful, so maybe you should go to Chicago to experience growth (or, at least, start a killer garden). And then there’s “all things know,” which is extremely vague and slightly ominous—it feels a little panopticon-y, which is not particularly ideal?
All in all: great song, terrible travel advice. If you’re debating the merits of a Chicago vacation, I think you might be better off just asking a travel agent, because if Sufjan Stevens has an opinion on the matter, he sure as hell makes it hard to discern in this song.
15. Hole: “Malibu”
“Help me, please / Burn the sorrow from your eyes / Oh, come on be alive again / Don’t lay down and die! / Hey, hey / You know what to do / Oh, baby, drive away from Malibu” → “Hey, hey / I’m gonna follow you / Oh baby, fly away, yeah, to Malibu / Oceans of angels / Oceans of stars / Down by the sea is where you / Drown your scars”
Man, does Courtney Love give us some mixed messages about Malibu here. The Malibu question starts out rather uncomplicated, with the song saying it makes one want to “lay down and die” and the only thing one can possibly do to save oneself is to “drive away from Malibu.” But this perspective shifts dramatically as the track continues: By the song’s end, it seems as if the only way to free oneself is actually to fly away to Malibu, and it’s only “down by the sea” in Malibu that you can “drown your scars.” The song’s opinion of Malibu has a whole arc, and while that’s cool and all, it seems a little weighty for a fun vacation. Sure, Love ends the song with a more positive outlook on the city, but to be honest, most people would rather spend their money, time and energy going somewhere that won’t require them to undergo a difficult slow-burn character development arc in order to enjoy their time there. So while I wouldn’t insist you avoid Malibu per se, I wouldn’t put it at the top of my list.
14. Johnny Cash and June Carter Cash: “Jackson”
“I’m goin’ to Jackson / And that’s a fact / Yeah, we’re goin’ to Jackson / Ain’t never comin’ back”
Honestly, this song—like the enigma that is both “Kyoto”s—leaves me with more questions than answers. Unlike the “Kyoto”s, however, I think most of us would feel a bit more hesitant about pursuing answers. To simplify things, let’s make a pros and cons list of Johnny and June’s perception of Jackson. Pros: It’s a good place to mess around; people will bow to you; women will want to have sex with you; you will never want to leave. Pretty good, right? But then there are the cons: It’ll wreck your health; you’ll make a big fool of yourself; everyone will laugh at you and lead you ‘round town like a scalded hound with your tail tucked between your legs. The cons, arguably, outweigh the pros here. But if you’re ever looking to go on a BoJack Horseman-style bender, Jackson sounds absolutely perfect. (If you’re fucked up enough, those weighty cons become pretty inconsequential, I’d imagine! That’s probably why the song’s speaker wants to go there so badly). Until then, though, I’d probably recommend skipping it.
13. Weezer: “Beverly Hills”
“Beverly Hills, that’s where I want to be / Livin’ in Beverly Hills, rolling like a celebrity”
Beverly Hills sounds pretty cool: Rolling like a celebrity? Being a movie star, so beautiful and clean? Living just like a king? Getting to be the next big thing? Hell yeah. Except that’s not actually achievable for most of us, Rivers Cuomo included—he says he doesn’t “stand a chance / It’s something that you’re born into / And I just don’t belong.” Cuomo is already way more famous than most of us will ever be, so if he’s a “no class beat down fool” who has to merely “watch the stars play” from his own little corner of the world, what the hell does that make us? So while Beverly Hills sounds great, it sounds like most of us probably could never actually live there, and most of us shouldn’t even try. But in the very off chance that a celebrity inexplicably has nothing better to do with their time than read this list, I will say that if you are rich and/or famous, and somehow aren’t living in Beverly Hills already, you might want to check it out.
12. The Magnetic Fields: “Washington, D.C.”
“Washington, D.C. / It’s paradise to me”
This song is actually extremely positive about Washington D.C., going so far as to say “it’s paradise to me.” So why is it so low on the list? Well, because the reason the song’s speaker loves the city so much is entirely irrelevant to the vast majority of people on Earth. Sure, Washington D.C. is great, but “Not because it is the grand old seat / Of precious freedom and democracy / No no no / It’s not the greenery turning gold in fall / The scenery circling the mall / It’s just that’s where my baby lives / That’s all.” Speaking for myself, here, but I do not have a baby (romantic), and if I did, I don’t think they’d be in Washington D.C., as I currently live in New York, so D.C. is very much beyond the 100 mile radius that most dating apps are limited to. I also do not have a baby (child), and again, if I did, they’d probably be with me, not in D.C. Also, I am 22 and really do not want a baby (child) right now. While you, the reader, are not me, there is a very high probability that you also do not have a baby (romantic and/or child) in Washington, D.C., because that is one city, and our world is very large. In other words, if your baby is in D.C., then hooey for you, go visit D.C. to your heart’s content, but also maybe consider how little the nation’s capital might appeal to those of us without babies there. It’s hard, being D.C.-baby-less. For those of us sans D.C. baby, it sounds like America’s capital city is an easy pass.
11. TIE: St. Vincent: “New York City” & Adrianne Lenker: “New York City”
St. Vincent: “New York isn’t New York without you, love / So far in a few blocks, to be so low / And if I call you from First Avenue / Well, you’re the only motherfucker in the city who can handle me”
Adrianne Lenker: “Well, New York City split me like a log in a mill / Half of me happy, the other half ill / But I feel myself a-warming to the old neon chill / I still feel a longing, but it’s chased by a thrill”
Much like Washington D.C., it sounds like the only real reason to go to New York is for one specific person, but unlike Washington D.C., there seem to be some merits to New York regardless (particularly in Adrianne Lenker’s song). Also unlike D.C., however, the person making the city worthwhile seems at once both more specific and more nebulous than one’s “baby.” Both Lenker and St. Vincent’s Annie Clark talk about the one person that makes New York worthwhile, but they never specify their relationship with said person—as such, I have come to the obvious conclusion that, while D.C. is made worthwhile by having a partner and/or child there, NYC is made worthwhile by the one specific person that both Lenker and Clark somehow seem to know (I don’t believe in coincidences, so it has to be the same individual, obviously). Frustratingly, neither song gives us any insight into who that person is, so unless either Lenker or Clark take pity on you and give you the person’s address so you can track them down, it sounds like you’d be pretty doomed in New York.
According to St. Vincent, the individual in question is apparently “the only motherfucker in the city who can handle me.” This is unfortunate for me, as someone currently living in New York. As I do not know who she’s speaking of, it appears there will not be anyone in the city who can handle me, and that kind of sucks. Lenker, however, is a little more mixed on New York than Clark, who seems to think the city’s only real boon is the mysterious individual at the song’s center. Lenker, on the other hand, believes New York is home to “the lowest lows and the highest highs” and is known to split people “Like a log in a mill / Half of me happy, the other half ill.” She does reach a positive conclusion about the Big Apple in the end, but the deciding factor is none other than that same enigmatic figure. Lenker says “it’s easy to lose your mind” in NYC, so much so that she might’ve lost her own if she hadn’t found the song’s subject, and similarly, that without seeing the subject’s face, she believes she never would have found her place. Again, given that neither songwriter gives us any clues as to who the miraculous “you” is that they speak of, I highly doubt you’d be able to find them in such a big city—meaning you stand a decent to high chance of losing your mind and never finding your place, neither of which are ideal circumstances for anyone to be in.
10. Phoenix: “Rome”
“Rome, Rome, Rome, Rome / Rome, Rome, Rome, Rome / Rome, Rome, Rome, Rome / Rome, Rome, Rome, Rome / Rome, Rome, Rome, Rome / Rome, Rome, Rome, Rome”
I feel like a city that’s used as a metaphor for the decay of a failed relationship might not be the most fun vacation spot. I mean, “Rome: Many tears have fallen here”? Yeesh, talk about a downer. That being said, Phoenix does hit on something crucial in this song: Rome is a really great name for a city and is fun to say many times in a row! In conclusion: Say the word Rome 24x fast, but probably don’t go there.
9. Billy Joel: “Vienna”
“Slow down, you crazy child / And take the phone off the hook and disappear for a while / It’s alright, you can afford to lose a day or two, ooh / When will you realize Vienna waits for you?”
For the easily overwhelmed among us (read: yours truly), Billy Joel’s Vienna sounds like Heaven. I can’t tell you how many times I’ve cursed the fact that I can’t just press pause on life and take a few days to collect myself, or to catch up on work, or even just to exist for a little bit with no responsibilities to weigh on me—and while that is technically impossible for everyone who is not Adam Driver in Megalopolis, it sounds like Vienna could very well be the next best thing.
However, as much as it may pain me to say this, I cannot encourage any sort of visitation to Vienna. Vienna runs the risk of functioning a little like the Island of the Lotus Eaters from Greek mythology. Even if it’s true that in Vienna “you can afford to lose a day or two” because “Vienna waits for you,” the fact remains that outside of Vienna’s borders, the rest of the world is continuing on, and that’s terrifying. I mean, if Vienna were to become entirely self-sufficient and cut off contact from the rest of the world, and if you were able to force all your loved ones to move there, then sure, I’d give it the green light. But let’s be realistic here—that is not particularly likely. As such, I cannot in good conscience tell you to do anything other than avoid Vienna entirely, because I fear that even a short vacation there might turn you into one of those pathetic people trapped in the Lotus Hotel from Percy Jackson who still think it’s the 60s or whatever, and man, that would suck.
“I’m sinkin’ down / Here darlin’ in Youngstown”
At least according to this song, there is quite literally nothing appealing about Youngstown (except I guess that it made the cannonballs that allowed the Union to beat the Confederacy, so there’s that, I suppose?). Unless you like nuclear warfare and being drafted to pointless wars, smokestacks and skies of soot and clay, and mills that build bombs, it really doesn’t sound like Youngstown has much to offer. Except, that is, for “sinkin’ down,” and that sounds pretty unpleasant, too. Thanks for the insight, Bruce; everyone, let’s pass on Youngstown.
7. Lucinda Williams: “Minneapolis”
“I’ve been waiting for you to come back / Since you left Minneapolis / Snow covers the streetlamps and the windowsills / The buildings and the brittle crooked trees / Dead leaves of December / Thin skinned and splintered / Never gotten used to this bitter winter”
Minneapolis sounds depressing, and quite possibly the worst place anyone with Seasonal Affective Disorder could go. Apparently, it’s all brittle crooked trees and snow covering everything, dead leaves and bitter winters, black clouds that cover up the sun, and also the desire to open up old wounds until you dye the snow-covered streets red with your own blood. Fun! However, it does sound like Minneapolis has precisely a dozen yellow roses. In fact, according to Lucinda Williams, those dozen roses are all that’s left in Minneapolis—but, I mean, that’s still something, I guess! So hey, if you want a dozen yellow roses, you know exactly where to head. Otherwise, don’t bother.
6. Built to Spill: “Twin Falls”
“Christmas, Twin Falls, Idaho / Is her oldest memory / She was only two / It’s the first time she felt blue… / My mom’s good, she got me out of / Twin Falls, Idaho / Before I got too old / You know how that goes”
How miserable does a city have to be in order to cement itself as your very first memory of feeling sad in your entire life? Pretty damn miserable, I’d bet. At least as Built to Spill tells it, Twin Falls sucks so much that some girl’s oldest memory is feeling blue there—and at only two years old, no less. Maybe I just don’t know a lot about toddler psychology, but I feel like most toddlers rarely feel “blue.” Angry? Upset? Wailing and bawling? Sure! But melancholic, blue? I don’t think so. Twin Falls must be real awful if it somehow forces a two year old to succumb to existential ennui, right? And if that’s not enough of a bad omen for you, apparently Twin Falls sucks so hard that getting your kids out of that town single-handedly makes you a good parent. Yikes.
5. The Mountain Goats: “Tallahassee”
“Half the whole town gone for the summer / Terrible silence coming down here”
“There are loose ends by the score / What did I come down here for? / You”
I’ll be upfront: I have a conflict of interest regarding this song. I was born and raised in Tallahassee, Florida, and have spent the vast majority of my life stuck there. As such, I can officially confirm that John Darnielle hit the nail on the head with this one. Ill-kept front yards? Check. Prop airplanes passing loudly overhead? Check. Prayers to summon the destroying angel? Check. Half the whole town gone for the summer? Terrible silence coming down here? Loose ends by the score? Check, check and check. “There is no schedule,” Darnielle sings, sadly. “There is no plan / We can fall back on.” This is very accurate. There is nothing to do in Tallahassee, especially when you’re a child and don’t even have a car, an identity I had for most of my time there.
After (aptly) listing the myriad depressing idiosyncrasies of Tallahassee, Darnielle croons: “What did I come down here for? / You.” It’s one of my favorite lines in any love-adjacent song; pure and sweet, understated and honest. I, perhaps unfortunately, do have a “you” in Tallahassee, just like the song’s speaker: My parents live there and I love them very much, so as much as I might groan about my hometown, I will always come back for them. What did I come down here for? Them. Unquestionably them.
That being said, most of you, surely, do not have a “you” in Tallahassee, and thus face a similar dilemma as with the Magnetic Fields’ “Washington, D.C.”—except that song had no critiques of its central city whatsoever, and “Tallahassee” is chock full of them. So: Do not go to Tallahassee. You will ask yourself what you came down here for, and you will not have an answer. I can’t avoid Tallahassee. “Tallahassee”’s speaker can’t avoid Tallahassee. But you can. Just keep that in mind.
4. Lily Allen: “LDN”
“There was a little old lady who was walking down the road / She was struggling with bags from Tesco / … / A kid came along to offer a hand / But before she had time to accept it / Hits her over the head, doesn’t care if she’s dead / ‘Cause he’s got all her jewelry and wallet”
Okay, yeah, the one line that explicitly says the word “London” in Lily Allen’s song is pretty inconclusive about the city itself (“You might laugh, you might frown / Walkin ‘round London town), but every other moment of the song rails against any positive notion one might have of England’s capital city. London might look nice, the song insists, “But if you look twice / You can see it’s all lies.” The song opens with the speaker biking through London and seething about how “the filth took away my license” but it’s fine, because now they get to see all the wondrous sights of the city up-close and personal. Over there, “a fella looking dapper, and he’s sitting with a slapper.” Oh, wait, nevermind; that’s “a pimp and his crack whore.” Aw, “a little old lady” trying to cross the street while holding Tesco bags and a kid helping her! Ah, shit, scratch that, he’s now hitting “her over the head, doesn’t care if she’s dead / ‘Cause he’s got all her jewelry and wallet.” I mean, Jesus. London sounds like Gotham or something, and instead of Batman, you only have…monarchical figureheads? Woof. Rough.
“Hollywood makes me wanna puke / Hollywood makes me wanna puke”
Self-explanatory.
2. R.E.M.: “(Don’t Go Back to) Rockville”
“Don’t go back to Rockville / And waste another year”
According to R.E.M. lore, Mike Mills wrote this song in 1980 for the sole purpose of convincing his then-girlfriend not to spend her summer in her hometown of Rockville, Maryland. I’ve got to wonder how she took the song—I mean, did she want to go home? Was this just a weird gaslight-y attempt from her boyfriend to get her to dislike her hometown enough to stay with him over the summer? Based on the song’s lyrics, that does sound possible: “You’ll wind up in some factory,” Mills sings, “That’s full of filth and nowhere left to go / Walk home to an empty house / Sit around all by yourself / I know it might sound strange but I believe / You’ll be coming back before too long.” He even tacks on a good ole “everyone hates you there” sentiment: “Everyone in town only wants to bring you down / And that’s how it’s supposed to be.”
I mean, based on this, I sure as hell don’t want to go to Rockville. But even though I’m not the biggest fan of my hometown, to say the least, I feel like I’d be a little bit peeved if I had a boyfriend who wrote me a song like this to try and get me not to go home for the summer. Like, really? You couldn’t just… talk to me about it? Or—I know this sounds crazy, but hear me out—respect my wishes on the matter? That’s really neither here nor there, though; this isn’t a “good boyfriend” list, it’s a “city-songs that talk shit about their cities” list, and yeah, this is quite the negative take on Rockville. It’s only natural that a song written for the express purpose of convincing someone to avoid its titular city tops the “songs that make me want to avoid their titular city” list—or, rather, it would top it, if not for “Portland, Maine” by Donovan Woods, which frankly makes this boyfriend’s reaction to his girlfriend’s desire to go to a song’s titular city seem downright reasonable.
1. Donovan Woods: “Portland, Maine”
“Portland, Maine, I don’t know where that is / And I don’t want to know”
Look. I’ve been to Portland, Maine, and I thought it was lovely! But that’s not the point of this list. When setting aside my own knowledge of Portland, I can safely say that it’s hard to imagine a song that hates its titular city as much as “Portland, Maine” does. The entire narrative of the song is basically just a dude ending a healthy, good relationship for the sole reason of not wanting to ever have to go to Portland. He even says, “I won’t pretend that I won’t miss [our relationship] / But Portland, Maine, I don’t know where that is / And I don’t want to know.” The speaker doesn’t even know where the town is, but apparently the mere thought of it is so appalling that he’s immediately willing to end a long-term relationship rather than even consider spending time there! “You can go ahead and hate me, that’s just fine,” Woods sings. “It doesn’t matter either way, I’m right.” Right about…Portland sucking?! That is the hill you’re dying on? I’m sorry, that’s just crazy. But hey, again, this isn’t a “sane reaction to your girlfriend’s favorite city” list, it’s an “I wouldn’t go to this city even when Hell freezes over” list. And boy howdy, does this one take the cake. So, stay the hell away from Portland, I guess. Damn.
