I'll Sink Manhattan: a piece of spiteful music genius

Why this TMBG track is a perfect break up song for broken hearts.

I’m writing about every song by They Might Be Giants. Join many others as I share about my life and love for this band, one song at a time. Subscribe Today.

---

Imagine a haunting melody, laced with spite. A phone ringing, unanswered. Faint backwards speaking. And then, a voice, singing with a beautiful, venomous precision:

“I'll sink Manhattan. 
Right under the sea. 
I'll find the sweetest spot to watch as it goes away.”

A Love Song for When Love Dies

Welcome to "I’ll Sink Manhattan" by They Might Be Giants—a love song that ends in apocalyptic revenge.

According to John Flansburgh, "I’ll Sink Manhattan" is a song “about falling in love, then falling out of love, and then killing everyone in Manhattan.” It’s the sixth track on Miscellaneous T, the collection of B-sides that I’ve been writing about for the last five weeks. And for me, it was yet another of my ultimate high school breakup anthems.

The High School Crush and Crash

Her name was Carly. She had red hair, a cute button nose, and the rare ability to make me laugh. I’d been absorbed into her friend group through my best friend, who’d known these people since junior high, while I was the outsider, tagging along as I started high school.

Carly and I became fast friends, and eventually, I gathered up the courage to ask her out. At that age, "going out" mostly meant holding hands at lunch and declaring our new relationship to our friends. Looking back, I realize that we were both still learning what it meant to care about someone—or at least to act like it.

A few weeks in, though, it all came crashing down.

When Your Friends All Know First

After lunch one day, Carly and I got up to walk to class. Our group trailed a few steps behind, and my best friend hung back with them. Suddenly, he called out to me:

"Wait, Chase! Nooooo!"

I glanced back, confused, as Carly tapped me on the shoulder. She was staring back at me with an expression reserved for parents who are about to tell their child that the family hamster died.

“I think we should just be friends,” she said.

“Oh, that’s… that’s okay,” I lied.

She apologized, and I mumbled some more lies about how it "felt right" to just be friends. She walked off to her class, and my best friend rushed over to explain that he found out the group had known about the impending breakup and they forced him to hang back so he tried to yell out and warn me.

The Little Green Box of Hate

The next day, nursing my wounded pride, I sat in my Careers class and folded an origami box out of green construction paper. On the outside, I wrote, Little Green Box of Hate: Do Not Open. Inside, I scrawled a message that would make it clear just how deeply I’d been wronged:

"You have just opened the little green box. An evil hatred has been released into your reality and can never be placed back inside. I'm sorry."

At lunch, I handed it to Carly. She opened it, read the message aloud, and looked stricken. My friends shot me a mix of scowls and walked away. In that moment, I felt smugly satisfied. My hurt had been transferred to her, mission “accomplished.”

It wasn’t exactly a mature way to handle things, but at the time, it felt like justice. And "I’ll Sink Manhattan"—with its promise to drown an entire city—was the perfect soundtrack.

The Sounds of Heartbreak

Musically, "I’ll Sink Manhattan" is a masterclass in sonic alchemy. Listening to it now, on my new AKG 702 headphones (thank you, birthday gifts), I can pick out each element that makes it so unsettlingly perfect. Let’s run them down:

• a phone ringing

• a sample of a string section

• a backwards recording of a message left by a NYC policeman left on the Dial-A-Song machine

• a backwards cymbal

• a sample of a typewriter

Add in Flansburgh’s “ohhh”s and “hey”s, layered as if they’re haunted echoes and chords, and you’ve got a song that feels as disorienting yet beautiful as heartbreak itself.

When Breaking Up Means Burning It All Down

"I’ll Sink Manhattan" isn’t just a breakup song—it’s a fantasy of total destruction as a coping mechanism. It felt validating then to hear someone give voice to those feelings in such an exaggerated way. As an adult, I recognize that sinking an entire city because of a breakup is not necessary (or possible.)

But sometimes, when a teenager’s world feels like it’s crumbling, they want everything else to go down with it. That’s what I love about this song. The band was able to channel absurdity and bitterness into something deeply cathartic.

"I’ll Sink Manhattan" remains one of They Might Be Giants' most unique creations—a blend of bitter humor, musical experimentation, and that dark catharsis you only get from truly spiteful art. If you’ve ever had a “little green box” moment, maybe it’s time to give this song another listen. Or tell me: what was your high school breakup anthem?

---

Want more TMBG in your life? Get posts delivered directly to your inbox each week for free by clicking the banner below.

BONUS STUFF!

Recently, TMBG released a live compilation featuring they’re latest horns ensemble called ‘Beast of Horns.’ The album is available on their website with some samples made available on streaming. The live horns version of I’ll Sink Manhattan is EPIC.