TDOH: Ranking the Characters of Hamilton

Note: Take a look at this post to know what I am trying to do with these posts over the next two weeks – and beyond!

The musical Hamilton is very fluid with some of the facts surrounding the man himself, and some of the choices that Lin-Manuel Miranda made in moving the timeline around a bit and making different people do the things that others did in real life help tell a better story. Two big changes jump out: Angelica Schuyler’s appreciation of Alexander Hamilton the man is presented as almost a missed connection in a sense, whereas in real life, she was already married with a couple of kids by the time that Alexander met Eliza. Second, the Reynolds Affair was discovered by James Monroe and a couple of others in real life, whereas the musical presents Aaron Burr, Thomas Jefferson and James Madison as being the prompt for the Reynolds Pamphlet.

But in this post, I want to rank the “main” characters in the musical, based solely on the songs they sing and all that (seeing as how I’ve yet to actually see the musical). The musical has four double-use roles, where the same actor plays a different character in Act 1 than they do in Act 2. I will be ranking the characters and not actors, so there are 14 total roles to rank, and like most ranking we’ll go in reverse chronological order.

Without further ado, the third Schuyler sister will start things off:

14) Peggy Schuyler – Young Peggy is only credited on one song – “The Schuyler Sisters” – the song that introduces us to the sisters that had a profound affect on the real Alexander Hamilton. Peggy is just a downer in this song, and doesn’t have much to do, so it is for this reason that she ends up last.

13) Hercules Mulligan – Maybe Mr. Mulligan is further developed during the actual musical, and he does have some great parts in the songs he is on – his return during “Yorktown (The World Turned Upside Down)” is pretty fun – but someone has to be slightly better than Peggy, and it almost defaults to Hercules Mulligan.

12) Maria Reynolds – In real life, Maria Reynolds (and her husband) were probably complicit in an extortion plot against Alexander Hamilton. This is depicted in the musical as well, and Ms. Reynolds’ song – “Say No to This” – really gets the point across that Hamilton is kind of scumbag regardless of the motives behind the affair. But like her alter ego in Act 1 Peggy Schuyler, Maria only has one entry in Act 2, so she’s pretty low on the list, which is more a product of all the great roles above her.

11) James Madison – James Madison doesn’t show up until the second act – he’s Hercules Mulligan’s replacement – and doesn’t have much to do other than follow Jefferson around and rail against all of Hamilton’s plans. But since he shows up all through the second act, he gets ranked a bit higher than the others.

10) King George III – Don’t get me wrong. King George’s three songs are some of my favorites, and if I was ranking songs, he’d probably end up higher on the list. But unless he actually shows up a bit more in the actual production, it doesn’t seem like he’s around all that much based on the soundtrack. My affection for his songs moves him up the list though.

9) Philip Hamilton – Honestly, he should probably be a bit higher, as his (spoiler alert) death is one of the most poignant moments in the entire thing. But unlike his alter ego (next up), he only gets half an act to make his impact.

8) John Laurens – The actor that plays John Laurens and Philip Hamilton has the pleasure of dying twice during the course of the play, but Laurens’ presence through most of Act 1 gets him the top spot of the bottom half of this list.

7) Marquis de Lafayette – The last split role also shares a spot on the list with his 2nd Act counterpart. The “Fighting Frenchman” has a lot to do in the first act, first as Hamilton’s friend and later as the replacement for General Lee at the Battle of Monmouth. He also convinces General Washington to bring back Hamilton from his self-imposed exile prior to the Battle of Yorktown, so that should be worth something too.

6) Thomas Jefferson – In your daily reminder that #JeffersonIsTheWorst, his depiction in the musical better aligns with the portrait painted of him in Chernow’s Alexander Hamilton. My sister mentioned how he was portrayed in 1776, which is a musical I sadly have not seen, making “him out to be a nice person and in reality he was terrible.” I’m glad the Hamilton depiction fixes this a bit, but he’s still not nearly as bad here as he was in real life. Too bad they didn’t include “Cabinet Battle #3” in the final version of the musical.

5) Angelica Schuyler – The second Schuyler sister of importance, Angelica is a huge presence in the first act, but she sails of to Europe and disappears for a lot of Act 2, only coming back after Hamilton has his dalliance with Maria Reynolds. Nevertheless, “Satisfied” is one of the best songs in the musical, and Renée Elise Goldsberry is amazing on the Original Cast Recording, even if she does occasionally sound like Phillipa Soo as Eliza Hamilton.

4) George Washington – It’s hard to say that Washington – both as a character and a real person – wasn’t an amazing presence. He gets this relatively lofty spot on this list for his farewell song alone – “One Last Time” – which uses the actual words from his Farewell Address. Plus, I really appreciate how the father/son relationship with Hamilton is presented, which aligns well with real life.

We’re down to the final three, and the order might be surprising, and it is probably where the most change will occur once I actually see the musical. Since these rankings are based solely on the soundtrack, however, this is how I rank the three most important roles:

3) Alexander Hamilton – The lead dude is not the best dude?!?! It is kind of surprising. Despite my affinity for Hamilton the man – still in second place behind my man Abraham Lincoln when it comes to Americans in history – he takes a secondary role to the two people ahead of him in the musical. He’s very important, don’t get me wrong, but as much as the story is about Hamilton, it is ultimately more about his interactions with his wife Eliza and his murderer Aaron Burr. Hamilton is simply the common thread that ties it all together, and the fact that the three best songs in the musical are given to Eliza or Burr should say something.

2) Eliza Hamilton – Listen to “Burn.” Or her reaction to the death of her son in “Stay Alive (Reprise).” Or her bringing the show to a close in “Who Lives, Who Dies, Who Tells Your Story.” Sure, they are the songs most likely to turn you into a blubbering mess, but they are all amazing. The real life Eliza was Hamilton’s staunchest defenders after he died, “telling his story” at every opportunity. This is in spite of Hamilton being a bit of a scumbag with the whole Maria Reynolds situation – there are letters he sent to her while she was away in Albany and he was messing around with Maria where he begged her to stay away – and she is probably the most responsible for later historians not simply discounting Hamilton’s presence as the guy that started a bank and died in a duel.

1) Aaron Burr – The main antagonist displays the most growth from beginning to end of the musical. He starts out seemingly skeptical of nearly everything that Hamilton does, eventually partners with him a bit after the Revolution when both were lawyers in New York City, makes Hamilton mad by running against his father-in-law (and winning) a Senate seat. And it all comes to a head when Hamilton endorses Jefferson over Burr in the election of 1800. The musical version of Burr also gets some of the best songs – “Wait For It”, “The Room Where it Happens”, “Dear Theodossia” (a nice duet with Hamilton about their kids), and “The World Was Wide Enough.”

In real life, it seems that they didn’t nearly interact all that much except in passing, but that would be a boring story. And it was Hamilton’s opposition to Burr in the race for New York governor in 1804. It was a culmination of decades of personal affronts, and both of the stubborn fools wouldn’t apologize for their behavior, culminating in the duel for which they are best remembered.

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Once I see the musical in a little over a week, I may come back and update the order a bit, but we’ll see. As any fan of musical theater knows – or fans of music in general – it’s often more about just the songs alone. That won’t stop me from writing another 1,500 words about it though.

Until next time…