Song of the Day #3,087: ‘Dear Theodosia (Reprise)’ – Hamilton Mixtape

hamilton_mixtapeWhen I first started listening to Hamilton, long before I knew I saw it on Broadway and before I knew it would become my whole family’s obsession, I was immediately drawn to the simple piano ballad ‘Dear Theodosia.’ It’s a love song from Alexander Hamilton and Aaron Burr to their young children and on of the prettiest songs in the play.

The track reminded me of Ben Folds’ ‘Gracie,’ one of my very favorite songs, and at the time I longed for a Ben Folds cover of ‘Dear Theodosia.’

Fast forward to the announcement of the mixtape, and lo and behold, it looked like my prayers had been answered! Not only would Ben Folds participate but his chosen track was none other than ‘Dear Theodosia.’ Cue giddy excitement!

But alas, it wasn’t meant to be. It turns out ‘Dear Theodosia’ is performed by Regina Spektor with an assist from Ben Folds that amounts to a couple of sung lines and maybe his piano accompaniment (though Spektor, too, plays the piano so it might be her). And while it’s a nice enough version, it was nevertheless a letdown.

But I got an unexpected treat in the mixtape’s final track, a reprise of ‘Dear Theodosia’ performed by Chance the Rapper with Francis and the Lights. Chance the Rapper’s raspy, imperfect vocals turn out to be just right for this emotional track. What a lovely surprise.

[Verse 1: Chance The Rapper]
Dear Theodosia, what to say to you?
You have my eyes. You have your mother’s name
When you came into the world, you cried and it broke my heart

I’m dedicating every day to you
Domestic life was never quite my style
When you smile
You knock me out, I fall apart
And I thought I was so smart

[Pre-Chorus: Chance The Rapper]
You will come of age with our young nation
We’ll bleed and fight for you, I’ll make it right for you
If we lay a strong enough foundation
We’ll pass it on to you, I’ll give the world to you

[Chorus: Chance The Rapper]
And you’ll blow us all away
Someday, someday
Yeah, you’ll blow us all away
Someday, someday

[Verse 2: Francis and the Lights & Chance The Rapper]
Oh Philip, when you smile I am undone, my son
Look at my son. Pride is not the word I’m looking for
There is so much more inside me now

Oh Philip, you outshine the morning sun, my son
And when you smile, I fall apart
And I thought I was so smart

[Bridge: Chance The Rapper & Francis and the Lights]
My father wasn’t around
My father wasn’t around
I swear that I’ll be around for you
I’ll do whatever it takes
I’ll make a million mistakes
I’ll make the world safe and sound for you…

[Outro]
We’ll make the world safe and sound for you
Someday
You will know you’re strong enough foundation
One day
Someday

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One thought on “Song of the Day #3,087: ‘Dear Theodosia (Reprise)’ – Hamilton Mixtape

  1. Dana says:

    I too would have liked to hear a full on Ben Folds cover of this song, but I enjoy the duet with Regina Spektor, and this reprise was unexpected and quite cool.

    Meanwhile, what truly must be noted and celebrated is the songwriting prowess of Miranda. The diversity of styles on display in Hamiltonall, so incredibly well executed, is just amazing.

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