The Hamilton Mixtape: A Track-by-Track Discussion

1.  No John Trumbull (Intro) by The Roots

This intro by The Roots captures the essence of the musical and these “inspired-bys and  covers” that make up the mixtape, all in less than a minute. You know you’re in for one hell of a ride, because this is not your usual staid John Trumbull depiction of the Founding Fathers.

2. My Shot (Rise Up Remix) by The Roots feat. Busta Rhymes, Joell Ortiz & Nate Ruess

When I first heard that Nate Ruess would be involved in the mixtape, I did a little dance of joy. And even if all I hear from him is the “whoa”s, it’s more than enough because his voice is angelic. It provides the perfect contrast to the amazing Busta Rhymes spitting out the, well, rhymes in his trademark staccato style.

3. Wrote My Way Out by Nas, Dave East, Lin-Manuel Miranda & Aloe Blacc

I had no idea Aloe Blacc would be in the album too. Another pleasant surprise. In this track that samples Lin-Manuel Miranda’s “Hurricane” from the cast album, he sings the hook and immediately it’s stuck in my head. Layered with Miranda’s freestyle verse and Nas’ closing spoken statement (which in itself is also a sample of Nas’ interview with Miranda for the Hamilton documentary), this track finally made me get how powerful a well-written and well-constructed rap song can be. Man, it’s good to hear Nas again! It’s just the third track, but it’s already an eye-opening moment.

4. Wait For It by Usher

Guys! Can I just pat myself on the back for this one? Usher covers Leslie Odom’s Aaron Burr number, and check this out – I wrote about the cast album last year, and this what I said about Burr:

Our main “villain”, if you will, is Aaron Burr who (SPOILER!) shot Hamilton in a duel. He’s a smarmy and opportunistic politician so his songs are mostly R&B-ish. Think Usher.

Can you believe that? I was referring to “Wait For It” in that statement. I’m horribly insecure about my lack of hip-hop knowledge, so this makes me feel validated. Good job, me.

5. An Open Letter (Interlude) by Watsky

After those explosive first four tracks (three if you don’t count the intro), we need a bit of a break. Enter Watsky’s rap about the John Adams pamphlet Hamilton wrote, and which was only referenced by the line “Sit down John, you fat mother…” in the musical. It’s almost a stripped-down track, with not a lot of instrumentation. By this point, I’m already amazed how such diverse artists can put their own spin on this material. The disgust that Hamilton felt for Adams was only hinted at in the musical, but Watsky’s interpretation puts a modern perspective on it. It would totally make sense if he were to release this as a stand-alone song about a beef he has with a fellow rapper.

6. Satisfied by Sia (feat. Miguel and Queen Latifah)

Oh. My. God. This was the second song I heard from the mixtape when they started teasing out tracks, and it blew me away. Sia’s vocals are so coolly calculating at first, then towards the end as her powerful voice cracks, she is able to evoke Angelica’s pain. Then Miguel comes in with just a few lines as Alexander Hamilton, but the way his voice drips like syrup all over the words “My name is Alexander Hamilton…unimportant, there’s a million things I haven’t done.” Angelica must have had a will of steel to resist that. Damn. Queen Latifah comes in to rap the verse, and you’re reminded how she was such a revolutionary in her day. Welcome back, Queen!

7. Dear Theodosia by Regina Spektor (feat. Ben Folds)

I stayed up to watch the live stream of the mixtape launch. Spektor came in right after The Roots sang the blistering “My Shot”, and as she did an almost straight cover, I thought it was a bit of a letdown. I love her, so I was expecting something more. Guys, I totally missed the point.  When I listened to the album in sequence, I remembered why I love Regina Spektor in the first place. She doesn’t need to mix up the song or produce a completely different version, because her quirky voice is more than enough to make it, as they say, her own. “Dear Theodosia” is a lullaby for a child, after all, and her singular voice has that indescribable pining quality that such a song needs. Ben Folds’ voice also has a similar effect, which makes him the perfect partner for Spektor. I’m sorry Regina! I still love you more than ever.

8. Valley Forge (Demo) by Lin-Manuel Miranda

One of the two demos included in the mixtape that didn’t make it to the show, this is an interesting insight into the whole process that brought us the cast album. You can recognize some of the verses that morphed into “Stay Alive”. Even for a demo, it still sounds complete and polished. As Miranda has said, they had to clean it up since he was sandwiched by legends.

9. It’s Quiet Uptown by Kelly Clarkson

Let me begin by saying that I love Kelly. Her songs are my anthems! But this just does not work for me. This song should be, well, quiet. Grieving. Sad. Haunted. Her voice is simply too strong and powerful to convey this moment of intense vulnerability and surrender. I had my misgivings when I read that she and Alicia Keys would be involved, because I figured it was just to make the album pop-py. Which this version turned out to be. This was the first song I heard off the mixtape, and I was intensely disappointed. For a long while I thought that the album would be a dud for me. Only Sia’s “Satisfied” made me excited again, and of course the whole album turned out to be great. Except this one song. I know everyone else is raving about it but God bless me I really can’t listen to it and I skip it every time.

10. That Would Be Enough by Alicia Keys

Suprisingly for me, I loved Alicia Keys’ version! I thought I would hate hers and love Kelly’s, but it was the other way around. Keys’ has quite a defined range, and together with her imperfect voice, it works to convey the longing and pleading in the text. She even does some soulful vamping towards the end, which is perfectly fine. I don’t hate it!

11. Immigrants (We Get The Job Done) by K’naan, Snow Tha Product, Riz MC & Residente

My heart went Boom! with this track. This is one of my absolute favorites: I love how Daveed Diggs’ line “Immigrants, we get the job done!” is used as the hook. Then that Spanglish rap, Riz MC’s accent and rhythm, the stuttering in the hook, what a mix. Then it ends with Chris Jackson’s powerful delivery of the line “Not yet” from “Yorktown”. This is intense.

12. You’ll Be Back by Jimmy Fallon

My initial reaction to this? Why does Jimmy Fallon have to be here? You can probably tell that I don’t like him all that much. But to be fair, King George does provide levity in the musical, so it makes sense that Fallon would do the job here. And also to be fair, because of his version I finally got all the British Invasion references they kept talking about when the cast album came out. I never could get why it “You’ll Be Back” was called Beatle-esque. I couldn’t think of a single Beatles song that it reminded me of (is it “For The Benefit of Mr. Kite”?), but Fallon sounds like a young McCartney here so I finally do get it. It’s a nice reprieve after “Immigrants”, I guess.

13. Helpless by Ashanti (feat. Ja Rule)

Oh boy! The second time my heart went boom. This version is the perfect throwback to the 90s R&B songs we loved so much, and those videos we used to see all the time back when MTV still played music. Ja Rule covering the song on which Miranda imitates him, it’s song-ception! Amazing. I can totally imagine someone singing about this guy they meet at a club, and someone tries to hit on them but you’re not having any of that – it’s totally a song that you could release today! This makes my inner eternal 90s kid incredibly happy.

14. Take A Break (Interlude) by !llmind

This is just a remix of Eliza’s “un deus trois” count-off, but it signals the point in the story when everything is about to fall apart for Hamilton. How can so much emotion be packed into 40 seconds?

15. Say Yes To This by Jill Scott

Jill Scott is an absolute goddess. This song, sung from the perspective of Maria Reynolds is an absolute gem. Her rich, soulful, come-hither voice is perfect. Some smart listeners have already pointed out that when you play this on top of “Say No To This” from the cast album, it reveals a whole new layer. This starts the trilogy of songs from the three women in Alexander’s life. Next up, Angelica.

16. Congratulations by Dessa

Dessa is appropriately livid as she crushes Hamilton in this track. With lyrics like

You have invented a new kind of stupid
A ‘damage you can never undo’ kind of stupid

she says the words we all want to say to Hamilton: how can you be so infernally stupid as to try to save your honor by besmirching your own name and your wife’s in the process? Why Alexander? What snapped in your brain? Why? Why? Beware a woman who is played, but even more beware of the sister of a woman who is played.

17. Burn by Andra Day

And lastly, Andra Day as Eliza. I think this is the only time you can use “slay” correctly, because that’s what she does. Building up from a tender start to an agonized crescendo, this has immeasurable heartbreak and shame and anger all over it. By the end of it, you feel as drained as Eliza.

18. Stay Alive (Interlude) by Stro Elliot

Those three songs are so heart-wrenching that we all need a break. Thank you Stro Elliot.

19. Cabinet Battle 3 (Demo) by Lin-Manuel Miranda

This is another treat for us as we hear the third Cabinet Battle about the proposed abolition of slavery that didn’t make the cut. I can’t imagine how it would have gone over with the audience if it had been included. The sparseness of the demo and the chime-like backing music echoes the danger of the topic and how it must have been such a difficult and delicate topic to even discuss with people like Jefferson and Washington who owned slaves. And so it ends with

Let’s hope the next generation thinks of something better

20. Washingtons By Your Side by Wiz Khalifa

As we wind down, we’re treated to Wiz Khalifa’s laid back yet oddly menacing song about starting from the bottom and making it to the top. I think it’s menacing because he completely flips the original song – he retains the melody and hook, but now it means something different. Which is a microcosm of the whole mixtape, I think. As we approach the end, everything is starting to come together and making sense as a whole concept.

21. History Has Its Eyes On You by John Legend

This is another one of my absolute favorites. John Legend elevates this track – which did not need any help, by the way – by making it a gospel song. He takes it to church and takes us along on this soaring journey. Chris Jackson’s original rendition deserves nothing less.

22. Who Tells Your Story by The Roots (feat. Common and Ingrid Michaelson)

Having heard only her ethereal collaborations with Joshua Radin, I had no idea Ingrid Michaelson could sound like this. It’s perfect that John Legend’s track segues to Common’s, since their differing styles shown back-to-back remind me of their Oscar-winning song “Glory” and how Common’s technique of slightly-behind-the-beat rapping is more like poetry than rap. By this point my mind is blown and I feel like a changed person just having listened to these songs.

23. Dear Theodosia (Reprise) by Chance The Rapper & Francis and the Lights

I never knew Chance The Rapper had a voice like this. It’s not fair to have this reprise as the last song. Just when you think you’re done running the gamut of emotions, he goes and takes out your heart and crushes it in front of you. Someone in the Hamilton fan group I joined pointed out that this is also the perfect song to sing to your pet, because you want to make the world right for them. Chance’s tentative vocals, far from perfect, juxtaposed with Miranda’s verse for Philip and the ending harmonies – I’m ugly crying at this point.

What a journey this mixtape is! It’s amazing how a group of such diverse artists can take all these songs and concepts that we know and love so well, and make something completely new and different. They made new songs about songs. With all the references to 90s music, it really is the perfect mixtape. Poor kids today will never know the feeling of putting together the perfect mixtape and giving it to someone you care about, carefully choosing the songs for them. And the feeling you get when someone gives you a mixtape, when they get the songs right and you know that they really get you? Wow. Thank you thank you, Lin-Manuel Miranda and everyone on this album. My heart is full.