12 ‘Hamilton’ songs that kept their staying power after years of listening

To the delight of obsessives everywhere, the movie of the musical Hamilton has finally hit Disney+. If you listen carefully, you can probably hear the sound of thousands of fresh Hamilfans being minted every day.  

To such newbies, those of us who’ve been listening to the soundtrack on heavy rotation since it was released in 2015 — one presidential administration and a lifetime ago — offer a very sincere and hearty welcome. If our experience is any guide, you’re in for years of pleasant re-watching and re-listening. Perhaps you too will dive into the Hamiltome, the book of the show, or the Ron Chernow biography that inspired it. Perhaps you too will love its twisty wordplay so much you’ll follow all the online breadcrumbs Lin-Manuel Miranda has left anyone looking for meanings and easter eggs.

What follows isn’t a ranking of the best songs in Hamilton; there are already plenty of those. (Personally I would top that list with “The Room Where It Happened,” which would put me at odds with the probable vote-winner, “Wait For It.”) Nor is it a list of the songs that sear themselves indelibly on a first listen (hard to top the raw energy of “Burn.”) 

No, these are the songs, in order of their appearance, that keep me coming back to the soundtrack five years after I first heard it (and four years after I first saw the show). These are the ones that didn’t necessarily hit right away and the tunes that have only gained in power the more I’ve learned about them. This is a love letter to the lines and scenes that still randomly appear in my head in the shower. Your mileage may vary, but for me, these are the soundtrack tunes with the most staying power when played on repeat.

1. “Alexander Hamilton”

The opening number isn’t just a great way to introduce newbies to the styles, scope, and speed of Hamilton. It’s also full of perspective-shifting moments that reward repeat listeners. 

For example, it took me a while to appreciate the  time-jump between the first two verses. The first reads like a resume: Struggling orphan writes about hurricane that hit his island, 18th century GoFundMe sends him to school on the mainland. This is Hamilton’s early life as he himself would tell it, full of braggadocio (“This kid is insane, man!”) and devoid of family. 

But the second scene, sung by Eliza, jumps back to fact check and fill in some painful gaps. Dude’s not really an orphan. His deadbeat dad left him (and is never mentioned again, which is just how Hamilton wanted it). His mom and cousin died in physical and mental torment, before his teens, before the hurricane. 

Almost everything in the rest of the story is foreshadowed in this tumble of words: Hamilton’s need for a father figure like Washington (and his anguish when Washington also splits); the importance of the hurricane letter to his self-image, leading to the disastrous Reynolds pamphlet decision; the muted grief over his mother that may have made him fight and/or bed everyone; and Eliza stepping in to reshape the narrative. 

We are left to wonder just how many of the million things we haven’t done will be unconsciously shaped by our childhood, no matter how much we strive to “be a new man.” And then the musical gets even more meta, referencing itself and questioning its own success in the final verse: “When America sings for you, will they know what you overcame?”    

2. “The Schuyler Sisters”

The first few New York songs, including the still-brilliant “My Shot,” wear their plot-packed meanings on their sleeve. But when Angelica, Eliza (and Peggy) Schuyler enter the scene, the whole musical’s perspective shifts again, in ways that require some unpacking. 

Aaron Burr, true to his dual nature, treats the sisters with both sneering condescension and flirtatious, dizzying rapport. It took looking the lyrics up on Genius before I caught the crucial extra comma in his line “I’m a trust fund, baby, you can trust me.” He’s not staking his own claim to wealth, he’s lying through his teeth in a very Trumpian manner: No one has a bigger fund of trust than I do.

But Angelica, true to her nature, shuts that shit down straight away. She’s here to talk books and politics, no matter what men may say about her doing so. “When I meet Thomas Jefferson, I’ma compel him to include women in the sequel” to the Declaration of Independence, she vows. 

It’s not just one of the biggest mic drops of the show; it also foreshadows something that happens years later, offstage. For in fact Angelica did meet Thomas Jefferson in Paris, along with the Marquis de Lafayette. The two men crafted The Declaration of the Rights of Man, a key document in the French revolution of 1789. And this time there was a sequel: The Declaration of the Rights of Women, which called out the original for its lack of equal treatment of the sexes.         

3. “Helpless”/”Satisfied”

Is it cheating to treat two songs as one? Not in the case of “Helpless” and “Satisfied,” which demand to be heard as a pair and cover the exact same events. Again, there’s a time jump backwards; again, it reveals the painful truth. The two songs are perfect  character-building yin and yang, and become more than the sum of their parts when you put them together. 

Indeed, they’re almost better listened to the opposite way around. Once you’ve fully ingested Angelica’s complex, fast-moving explanation of what really happened in those three minutes at the winter’s ball in 1780, then the bouncy love-song simplicity of “Helpless” becomes almost unbearably ironic. I also get chills at Hamilton’s casual foreshadowing when he tells Eliza “We’ll get a little place in Harlem and we’ll figure it out” — two things they wouldn’t do until after their son’s untimely death.  

4. “Dear Theodosia”

Call it Hamilton‘s sleeper hit: A deceptively simple lullaby that also contain the seeds of unbearable tragedy. Hamilton hopes that his newborn son Philip will “blow us all away” when we know the kid is going to die in a duel in Act II, just after that line is re-used to showcase his promise. Burr serenades the babe who bears her mother’s name; left unspoken is the fact that the elder Theodosia will die shortly after. (It’s hinted at just before the Burr-Hamilton duel, in Burr’s line “this man will not make an orphan of my daughter.”) 

An early preview version of Hamilton included an extra verse of “Dear Theodosia” where Burr is grieving his wife. It was a good cut, leaving us to twist the knife in our own hearts when we read up on Burr’s history. Also wisely cut from the soundtrack is another knife-twisting scene at the end of the song, one that reveals that Hamilton’s comrade (and possible lover) John Laurens has been killed in action. When soundtrack obsessives see that scene in the show, it blows us all away.    

5. “Non-Stop”

After Laurens’ death, Hamilton leaps into action. The years tumble away in this densely-plotted Act I closer. He and Burr defend Levi Weeks, the first accused murderer tried in the U.S., then Hamilton proposes his own Constitution (which included, the show doesn’t mention, the concept of an American king), then he defends the actual compromise Constitution in 51 tirelessly written Federalist Papers. 

It’s all a bit much on first listen, which is by design. Hamilton’s whole damn life is a bit much. Miranda brilliantly weaves together overlapping reprises of “Wait For It,” “Satisfied,” “History Has Its Eyes on You” and “Alexander Hamilton” while simultaneously introducing another refrain which will echo through Act II: “Why do you write like you’re running out of time?” 

The answer, of course, is because he was. Because we all are. But songs like this galvanize our remaining days and nights, reminding us to pack in as much as we can.   

6. “Take a Break”

The sign of a song with true staying power is that it doesn’t sound like much at first, but sends shivers down your spine when you pull out all the references on later listens. Here, in what seems like a dull domestic scene, we have Philip practicing French at the piano, using what we know to be his last words. Meanwhile his dad is upstairs writing slyly sexy letters to his sister-in-law, including the second crucial comma of the show in “my dearest, Angelica.” Miranda has called this true historical fact of their correspondence “comma sexting.” 

What else? So, so much. There’s the Macbeth meta-joke, which echoes an episode of the BBC comedy Blackadder. We think the show is going to observe the traditional stage taboo of not naming the “Scottish play,” then Hamilton goes ahead and blurts out the M-word anyway. Typical Hamilton. Later in the song, you can hear Angelica clapping back with a Lady Macbeth quote: “Screw your courage to the sticking place.”

Unspoken tragedy is back-shadowed as well as foreshadowed. Listen to that gap when Angelica arrives, in a reprise of “The Schuyler Sisters” — there’s no “and Peggy” this time because Peggy has died, again offstage. And oh, the sadness in that beautiful violin at the end, when Hamilton is left at home alone. It’s the perfect lead-in to the ominous opening of “Say No to This.”     

7. “The Room Where it Happens”

What else is there to say about this show-stopper, surely the funkiest tune this century to use a banjo? Start with the meta-reference: “show-stopper” is one translation of “pièce de résistance,” giving Burr’s use of that phrase a double meaning. End with the fact that the tangle of double meanings is what tips Burr over the edge into political megalomania. 

He’s made nakedly ambitious by not knowing, by FOMO. When John Bolton stole the title for his tell-all book on Trump, for which Miranda rightly slammed him, he really didn’t think about what kind of character he was referencing. 

The story in-between, of how the location of Washington, D.C. was traded for the concept of federal securities, may need time to marinate in your brain. But I promise it never gets old. Here is one of the best history lessons you can get in five minutes — not just because it lays bare the art of backroom dealing, but also the total lack of trustworthy contemporary sources, a problem historians have to deal with all the time. “The Room Where It Happens” is critical thinking you can tap your feet to. 

And once you’ve seen the stage show, in which the three inhabitants of the room face away from the audience, their wigs like featureless horror-movie faces, you’ll never forget that image.   

8. “Washington On Your Side”

What never gets old in this track is the flawless harmonizing, killer rhymes, and bouncy hip-hop beat. But it’s also a legacy of the time in which it was written. Jefferson, Madison, and Burr talk just like Tea Partiers outraged by Obamacare. They can’t get over their sense of personal injury after political defeat. These “Southern motherfucking Democratic-Republicans” have cropped up time and time again in American history under different names. 

Then too, there was generalized fury that the Bill of Rights (“which I wrote!” fumes Madison) was being trampled on, though how it was being trampled on is never specified. There’s just exaggeration and whiny victimhood, dressed up with quotes from Isaac Newton. The blame game keeps coming back to Hamilton and Washington’s friendship in the same way Trump’s finger always points, eventually, at his more-popular predecessor. At least in Hamilton, the victimhood is sung beautifully. 

9. “Hurricane”/”The Reynolds Pamphlet”

Again, I think it’s fair to treat these two songs as a unit that is better than the sum of its parts — you can’t understand one without the other. “Hurricane” gets more spellbinding every time you listen to it, especially after seeing the staging (Hamilton’s office goes flying in slow motion around him). You will be teasing meaning from that “I couldn’t seem to die” line over dozens of re-listens. 

But as great as ‘Hurricane’ is, it functions best as the build-up to Hamilton’s spectacularly self-sabotaging decision to publish the Reynolds Pamphlet. Just listen to the chorus trying to be the better angels on his shoulder as dark clouds gather: “Wait for it, wait for it! History has its eyes on you!” If only he’d be as cautious as Burr was, or as mindful as Washington. 

I have listened to “The Reynolds Pamphlet” repeatedly during the Trump administration. Every time, I think back to the weekend Miranda hosted Saturday Night Live in October 2016, the weekend of the Access Hollywood tape. “Never gonna be president now,” Miranda ad-libbed in front of Trump’s signed picture at the SNL studios. 

So yeah, arguably, this song is now more than the sum of its parts in another way, too. It is a permanent musical monument to the hubris of two well-meaning men.     

10. “It’s Quiet Uptown”

The staying power of this one is in its emotional truth, its ultimate catharsis, which just seems to build with every re-listen. If you weren’t moved to tears the first time around, don’t worry. The waterworks are coming. 

It’s kind of hard to navigate the moment Eliza finally speaks, followed by the choir’s “Forgiveness!”, without choking back a hot blubbery mess of emotions. When you learn it was developed around the same time the original theatre’s director was struggling with the death of his own child, the mess just gets hotter and blubberier. 

11. “The Election of 1800”

This perfectly-timed antidote to the “Uptown” blues deserves to be considered on its own merits, which don’t net it a spot on many ‘best of Hamilton‘ lists. But this witty little tune is far from just the bridge that gets us to the Hamilton-Burr duel. It builds to a titanic finale of its own, and along the way it manages to satirize electoral politics then and now. 

The election of 1800 was one of the weirdest in American history, with the possible exception of the election of 2020. It didn’t happen the way Miranda tells it: Burr was running as Jefferson’s VP on the same ticket, and only showed his ambition to be president himself after the election was deadlocked in the House of Representatives. The importance of Hamilton’s intervention is also exaggerated. 

But it’s exaggerated with great effect. It’s clear Miranda is giving us a whimsical fantasy election in which door-to-door campaigning and the say-nothing “listening tour” is invented, and Burr momentarily forgets that women can’t vote yet. I also never fail to chuckle at the voter who invents this modern cliche of relatability: “[Burr] seems approachable? Like … you could grab a beer with him …”

12. “Who Lives, Who Dies, Who Tells Your Story”

As with “Uptown,” the closing track gains an improbable amount of emotional strength with every listen. Not so much the part where Hamilton’s former enemies lionize him, but the part where it becomes Eliza’s story — and starts time-traveling again, tumbling forward 50 years. It’s not enough. I simultaneously hate this song for tearing my heart out, and would also pay to see an entire musical based on it. 

The heart-ripping commences with the key change, and reaches maximum effect with “the orphanage!” How can this line still catch in my throat even now; why does it still get dusty in the room after hundreds of re-listens? Even after a group of friends on a wild night at San Diego Comic-Con ran around the city singing it, mocking it, doing all we could to divest its emotional power? 

God only knows, but it’s a testament to how much this entire musical sticks in the soul long after the applause has faded.