10 Musical Theater Rap Songs from the Last 58 Years

Ever since I wrote my previous post on theater and rap, I’ve had song titles swirling around my head. I decided to put them all in an ordered, to get a more big-picture chronological view of musical theater rap through the years, and I thought I’d share that list with you.

1. “A Hymn to Him” from My Fair Lady (1956)

The character’s unappealing worldview notwithstanding, this is a great song, and a great performance by Rex Harrison. I haven’t seen the sheet music, so I don’t know how much of this is written to be sung and is spoken here by Harrison’s choosing, but boy, does he sell it as a spoken word piece.

Watch this video on YouTube.

2. “Rock Island” from The Music Man (1957)

I talked about my obsession with the same show’s “Ya Got Trouble” in my last post, but this is probably Meredith Willson’s real spoken word masterpiece. Stephen Sondheim once called it “surely one of the most startling and galvanic openings ever devised.” High praise, yes, but well deserved, if you ask me.

Watch this video on YouTube.

3. “Enterprise” from Runaways (1978)

This is one of the earliest musical theater songs that I would actually classify as rap—note that I described the previous two as “spoken word.” Runaways isn’t a very widely known musical, but this song is worth knowing for sure, and there’s some interesting discussion going on in the YouTube comments about early rap.

Watch this video on YouTube.

4. “The Witch’s Rap” from Into the Woods (1987)

In the introduction to his book Look I Made A Hat, Sondheim says this about incorporating rap into his work: “not until rap became omnipresently popular did I try to make it work: I imitated it in a passage for the Witch to sing during the opening number of Into the Woods. But I was never able to find another appropriate use for the technique, or perhaps I didn’t have the imagination to.” This sure seems imaginative enough to me, Mr. Sondheim.

Watch this video on YouTube.

5. “Today 4 U” from Rent (1996)

A fabulous rap, and a fabulous story song. There is an Akita named Evita. Enough said.

Watch this video on YouTube.

6. “The Cop Song” from Urinetown (2001)

This is a super catchy song, and also a middle school obsession of mine. Just imagine thirteen-year-old me, wagging my finger at my mother and rhythmically chanting, “Don’t be like them, don’t be like them, don’t be like them!” It was exactly as nerdy as it sounds.

Watch this video on YouTube.

7. “Great Big Stuff” from Dirty Rotten Scoundrels (2005)

A friend and I had a debate as to whether Norbert Leo Butz is really speaking or singing in this song, but it’s close enough to rap for my purposes. Apologies for the terrible video quality; Butz’s performance is too incredible for me to use any other version.

Watch this video on YouTube.

8. “In the Heights” from In the Heights (2008)

Hearing this song for the first time, and being ushered into the world of this show, was a completely magical theatrical experience. I can’t quite find the words to describe how much I love this song, so I’ll just let it speak for itself.

Watch this video on YouTube.

9. “Living the Dream” from Tales From the Bad Years (2009)

We’re nearing the end of our journey through time, and entering the territory of New Musical Theatre. Here’s a hilarious song by Kerrigan-Lowdermilk. Apropos of nothing, I find it especially amusing that Greg Hildreth sings about his hair being “gelled back” when actually it’s standing on end.

Watch this video on YouTube.

Bonus: “Def Ass Musical Theatre Gangsta Jam” by Kooman and Dimond (2011)

I count this as a bonus because it’s not from a musical, but I had to include it because 1) It’s written by NMT’s own Kooman and Dimond and 2) It’s too great to leave out. I promise, if you’ve never heard it before, it’s about to become your new jam.

Watch this video on YouTube.

That’s all I’ve got for now. If your favorite musical theater rap song isn’t included here, I want to hear about it!

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