There are very few musicals I can listen to without eventually needing a break, but Hamilton has somehow managed to avoid that fate.
Between the intricate lyricism, overlapping storylines, historical references, and characters who somehow make eighteenth-century political disagreements feel like modern-day drama, I find myself coming back to it again and again.
It’s one of those musicals where the more you listen, the more you notice. A lyric you overlooked the first ten times suddenly means something entirely different, or a character you initially dismissed becomes someone you find yourself defending. And, as someone who has spent a questionable amount of time listening to the soundtrack, I have naturally started imagining these characters outside the world of Broadway.
More specifically, I started wondering what they would sound like if they existed in today’s music industry.
Not necessarily who would play them in a Broadway revival, but which contemporary artists capture their personalities, emotional contradictions, and musical identities. Because as much as Hamilton is rooted in American history, its characters experience things that are hardly exclusive to the eighteenth century.
They want recognition. They want to fall in love and make questionable decisions. They hold grudges and occasionally let their egos get the better of them. Frankly, some of them would fit right into today’s music scene.
Aaron Burr
If there’s one character whose internal contradictions could easily find a home in contemporary R&B and hip-hop, it’s Aaron Burr.
On the surface, he presents himself as calculated, composed, and careful with his words. But beneath that restraint is someone who wants to be recognized, included, and given the opportunity to matter. That tension becomes especially clear in “The Room Where It Happens.” For Burr, the frustration isn’t that Hamilton gets what he wants; it’s that the important decisions are being made without him. He wants access to the room, but deeper down, he wants a say in what happens inside of it.
That’s where I see a connection to Drake.
Songs like “Trust Issues,” “Jungle,” and “Marvins Room” often explore the complicated space between wanting emotional connection and struggling to trust it. There’s vulnerability in Drake’s music, but it’s rarely presented without some degree of defensiveness, jealousy, or pride. Much like Burr, he can come across as controlled while revealing that there’s considerably more going on underneath.
I also think it’s important not to overlook Burr’s role in “Washington on Your Side.” He’s not simply standing around watching Hamilton succeed; he’s actively participating in political alliances with Jefferson and Madison, united by their frustration with Hamilton’s growing influence.
Then, by the time we reach “Your Obedient Servant,” the carefully maintained politeness between Burr and Hamilton has practically become their weapons. Their formal correspondence turns into a confrontation neither seems willing to walk away from. Burr’s restraint doesn’t mean he lacks ambition or anger. It means those feelings have been building for a long time.
Drake’s music captures a similar tension between composure and vulnerability, particularly when pride gets in the way of what someone actually wants to say. Neither is particularly easy to read, and that might be exactly the point.
Thomas Jefferson
Now, this is where things get interesting. If Burr is Drake, then Thomas Jefferson is Kendrick Lamar.
And before anyone questions how I managed to put two characters who collaborate in Hamilton alongside two artists known for one of the most publicized rap rivalries in recent music history, I promise there’s a reason.
Jefferson’s entrance in “What’d I Miss?” immediately establishes him as someone who enjoys an audience. He’s confident, theatrical, and very aware of the impression he makes. His personality is practically built for a stage. But Jefferson isn’t just there for the performance.
In “Washington on Your Side,” and both Cabinet Battles, he demonstrates how much he enjoys a public disagreement, especially when he believes he has the upper hand. The Cabinet Battles are particularly interesting because they turn political arguments into performances. The audience isn’t just listening to the arguments; they’re watching two people compete for influence through language, timing, and delivery.
That’s one reason Kendrick Lamar feels like such a fitting comparison. His music is built around precision, layered storytelling, and an unmistakable command of performance.
Songs like “HUMBLE.,” “DNA.,” and “Not Like Us” demonstrate different sides of that confidence. Kendrick knows how to make a statement, and he knows how to make an audience pay attention to it.
His 2025 Super Bowl halftime performance brought that ability to one of the largest stages in entertainment. With songs including “DNA.,” “HUMBLE.,” “euphoria,” and “Not Like Us,” he turned the performance into another moment that brought his rivalry with Drake into the public conversation.
The comparison becomes even more entertaining when we return to Burr. In Hamilton, Jefferson and Burr find common ground in their frustration with Hamilton and work together in “Washington on Your Side,” and then become alienated when they run against each other for office. In today’s music industry, counterparts are on opposite sides of a very public rivalry.
Of course, I’m not suggesting that Jefferson and Kendrick share the same beliefs, or that Burr and Drake are interchangeable people. The irony is simply too good not to appreciate. The two characters who join forces in the musical become two artists whose names have become closely associated with major musical feud. If nothing else, I think Lin-Manuel Miranda would appreciate the drama.
Angelica Schuyler
Moving from political rivalries to complicated feelings, Angelica Schuyler and SZA make a connection that feels almost too natural.
Angelica is one of the most intelligent and self-aware characters in the musical, but I think what makes her especially interesting is that her intelligence doesn’t make her immune to emotion. She understands the decisions she makes, even when those decisions are difficult.
“Satisfied” is probably the clearest example of this. The song takes us back through the wedding scene and allows Angelica to tell us what was happening beneath the surface and before the “I Do’s.” It’s not just a song about romantic feelings; it’s about recognizing what you want, understanding what you cannot have, and making a decision that you may have to live with long after the moment has passed. The structure itself makes the song so memorable. We have already watched the wedding happen, but suddenly we’re seeing when the two people meet through an entirely different perspective.
I see some of that emotional complexity in SZA’s music, particularly in “F2F,” “Love Me 4 Me,” and “My Turn.” What stands out to me about “My Turn” is its sense of empowerment. It reminds me that women can know exactly what they want without necessarily knowing how they are going to get there. There’s something powerful about that distinction. We don’t always have to have a perfectly mapped-out plan to recognize our own worth and decide that it’s our turn to pursue something more. That feeling connects with Angelica in a way I find especially meaningful.
She knows what she wants, understands the sacrifices involved, and still has to navigate a world where her choices aren’t always simple. And keep in mind, this was before people could block people.
Even Angelica’s smaller moments deserve attention. Her reaction in “The Reynolds Pamphlet” reminds us that she isn’t simply an observer of Hamilton and Eliza’s relationship. She has her own emotional investment in the people involved. And in “Take a Break,” we see another side of her: the sister who wants Hamilton to step away from his work and spend time with the people who care about him. Angelica isn’t defined by one romantic decision. She’s a sister, a thinker, a woman with her own ambitions, and someone who understands that being intelligent doesn’t mean having every feeling neatly figured out.
Don’t get me started with her obsession over commas.
Eliza Schuyler
If Angelica represents the complicated feelings we sometimes understand but cannot act on, Eliza represents what happens when those feelings become impossible to ignore.
I think Lizzy McAlpine is an especially fitting comparison because her music often feels intimate, almost like someone has opened a journal and decided to let the rest of us read it.
Eliza’s character is sometimes reduced to her relationship with Hamilton, but I’ve always found that interpretation incomplete. Yes, her relationship is central to her story, but she has an identity beyond being the person that Hamilton hurts.
In “Take a Break,” we see her asking for something incredibly ordinary: time with her family and a husband who is actually present. While Hamilton is constantly thinking about his work, his reputation, and what he will leave behind, Eliza is trying to remind him that there’s a life happening right in front of him.
That desire for connection is something I hear in McAlpine’s “Pancakes for Dinner.” There’s something particularly meaningful about the way ordinary moments can become the most important parts of a relationship. Her songs “Pushing It Down and Praying” and “doomsday” also explore emotional experiences that are difficult to neatly resolve. There’s tenderness, but there is also hurt, uncertainty, and the lingering weight of things left unsaid.
Then there’s “Burn,” which might be one of the most important moments in Eliza’s character development. After discovering Hamilton’s betrayal, she makes a decision about what parts of herself and her story he is allowed to keep. She doesn’t simply accept what has happened or quietly move forward. She takes control of the narrative and the only way she can at the moment, which believe me, is quite hard for her.
And, of course, we cannot talk about Eliza without talking about “Who Lives, Who Dies, Who Tells Your Story.” By the end of the musical, she has become the person who actively preserves the stories of those around her. She spends years making sure people are remembered, including her son by establishing the first private orphanage in New York City.
There is something especially fitting about pairing her with a songwriter whose music often feels like an act of preserving a moment before it disappears. Eliza’s story is not just about what she endured—it’s about what she chose to do with the life she had after being given more time.
King George III
And then, because every story needs someone who is a little dramatic, we have King George III. I genuinely cannot imagine leaving him out of this conversation. He is one of the most entertaining parts of Hamilton, largely because his songs interrupt the political tension with a completely different kind of theatrical energy.
“You’ll Be Back,” “What Comes Next?,” and “I Know Him” each gives us another glimpse into his personality. He’s smug, possessive, and almost hilariously convinced that everyone will eventually come around to his way of thinking.
The songs are written with such an exaggerated sense of confidence that it becomes part of the joke. He isn’t necessarily aware of how ridiculous he sounds, but he sure knows how to stand directly center stage with his staff and his eyes.
Chapell Roan feels like a fun contemporary counterpart because of her theatricality and her ability to make a musical persona feel like an entire world.
Songs like “Casual,” “Picture You,” and “The Subway” move through different emotional registers, but they all leave room for a strong sense of performance and personality. Chappell knows how to make a song feel like a scene, and I think King George would appreciate that.
The comparison isn’t necessarily about the subject matter of the songs. King George’s music is a comedic portrayal of royal entitlement and the crown’s refusal to accept the colony’s independence, while Chappell’s songs explore very different personal experiences.
It’s more about the commitment to theatrical expression. Both understand that sometimes the performance is just as important as the message. And honestly, I think King George would have a lot to say about Chappell’s stage presence. Whether she would want to hear it is another conversation entirely.
I think this is all part of what makes Hamilton so easy for me to return to. Every time I listen, I find another detail, another character moment, or another line that changes how I understand the story. The music makes history feel less distant and the people behind it feel a little more human.
If these characters ever did find themselves in today’s music industry, I have a feeling they would have plenty to say. Some would release an album, some would start a feud, and King George would demand a solo tour immediately.