Since its debut in 2015, Hamilton has captured the hearts and minds of audiences worldwide with its unique blend of hip-hop, history, and unforgettable storytelling. That and the fact that no one stops singing. While other musicals rely on dialogue to string their music together, in Hamilton, the music is the dialogue between characters and between characters and their better selves. Heck, it’s good enough to make other musicals seem less musical by comparison.
While there are countless articles ranking the best songs from the show, let’s take a different approach and explore the enduring staying power of ten exceptional tracks that continue to captivate listeners even after years of repeat performances.
1. Alexander Hamilton
The opening number of Hamilton isn’t just an introduction; it’s a lesson in storytelling. This track provides a glimpse into the life of the Founding Father, but it’s the subtle time-jump between verses that rewards repeat listens. As we hear about Hamilton’s early life with bravado, Eliza’s verse offers a poignant contrast, revealing the harsh realities of his childhood. This song lays the foundation for the complex themes that will unfold throughout the musical.
2. The Schuyler Sisters
When Angelica, Eliza, and Peggy Schuyler enter the scene, the musical takes on a new perspective. Aaron Burr’s interactions with the sisters are filled with intrigue, and a careful listen reveals subtle wordplay, such as the clever use of commas in “I’m a trust fund, baby, you can trust me.” — something later repeated in “Take a Break” (“My dearest, Angelica, with a comma after dearest.”) where Angelica points out how Hamilton seems to be developing feelings for her…or at least, that she thinks he is. Knowing Hamilton, though, that definitely could not have been a mistake.
Angelica’s determination to “compel [Thomas Jefferson] to include women in the sequel” foreshadows history’s unfolding, making this song a dynamic addition to the soundtrack.
3. The Twin Songs: Helpess and Satisfied
These two songs, while covering the same events, are best appreciated together. Angelica’s rapid-fire narrative in “Satisfied” adds depth to the sweetness of “Helpless.” Listening to them in reverse order creates an ironic twist, as we know that the blissful love story will soon be overshadowed by tragedy. These tracks highlight the complexities of the characters and the consequences of their choices.
4. Dear Theodosia
This understated lullaby carries the weight of foreshadowed tragedy every time Hamilton mentions falling apart for his son. Later in the musical, “Take a Break” brings back the duel motif as Philip plays the piano with Eliza. Later again, in “Blow Us All Away,” Philip mentions his father wanting Philip to be a better man than he is, a desire that leads to his death.
Hamilton’s hopes for his newborn son, Philip, contrast with the grim knowledge that the child will meet an untimely end in a duel. Burr’s serenade to his own daughter, also named Theodosia, adds another layer of melancholy to this beautiful yet haunting song.
After the death of John Laurens, Hamilton’s life takes a whirlwind turn. This densely-plotted Act I closer showcases Hamilton’s relentless ambition and the passage of time. It weaves together familiar refrains and introduces the question, “Why do you write like you’re running out of time?” This song reminds us of the urgency that drives the characters and encourages us to make the most of our own time.
6. Take a Break
This seemingly ordinary domestic scene conceals layers of references that become more apparent with each listen. From Philip practicing French (his last words) to Hamilton’s flirtatious letters to Angelica, the song is a treasure trove of hidden meanings. It also contains nods to Macbeth and hints at offstage tragedies, all while setting the stage for “Say No to This.”
7. The Room Where It Happens
This show-stopping number stands out with its funky banjo and catchy rhythm. Beyond the music, it delves into the theme of political ambition and the consequences of not being “in the room.” The song’s historical context, where the location of Washington, D.C., was traded for federal securities, offers a captivating history lesson wrapped in toe-tapping music. The stage production adds an unforgettable visual element as the characters face away from the audience, their wigs like featureless masks.
8. Washington On Your Side and One Last Time
This track combines flawless harmonies, clever rhymes, and a lively hip-hop beat. It also serves as a commentary on political discontent, echoing modern frustrations with a satirical twist. Jefferson, Madison, and Burr’s grievances and exaggerations resonate with political discourse of both the past and the present.
But then, it turns out Washington won’t always be on Hamilton’s side. “One Last Time” acts as a touching goodbye from Washington to Hamilton, to the nation, and to the audience. It’s also a glimpse at the kind of life Hamilton could have had if he wasn’t so stuck in his ways. Plus, all the lessons that Washington learned with age that Hamilton simply couldn’t bring himself to understand.
9. Hurricane and The Reynolds Pamphlet
These two songs are intertwined, each enhancing the other’s impact. “Hurricane” is spellbinding, with imagery that deepens with every listen. It builds up to Hamilton’s ill-fated decision to publish the Reynolds Pamphlet, showcasing the chorus’s internal struggle and foreshadowing the consequences of Hamilton’s actions. “The Reynolds Pamphlet” gained particular relevance during the Trump administration, serving as a lasting testament to the pitfalls of hubris.
10. It’s Quiet Uptown
This emotionally charged song gains power with each listen, leading to an inevitable catharsis. Eliza’s forgiveness and the choir’s plea for it create a poignant moment that is impossible to experience without feeling deeply moved. The knowledge that this song was developed during a time of personal tragedy for the show’s director adds an extra layer of poignancy.