The Spin on Original and Sampled Tracks

Hosts, Joe Watson and Toby Brazwell, connect the musical dots between legendary tracks and the often lesser-known songs they sampled. Uncover how these epic songs borrow from music of the past, enriching the musical landscape for generations to come.

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The Hamilton Hip-Hop Mixtape

| S:1 E:8

Hamilton, the theatrical powerhouse and a fixture of contemporary American culture, is the spotlight of Riffs on Riffs episode eight. This collision of American history, rap and hip-hop infused musical phenomenon, won 11 Tony awards in 2016 and continues to sell out shows across the United States. Joe and Toby enthusiastically explore Hamilton creator Lin-Manuel Miranda’s musical inspiration and how the songs and artists he grew up listening to are directly referenced throughout the show. As Mr. Miranda pays homage to the hip-hop greats, we too, celebrate the wonders of music sampling that created this miraculous thing called Hamilton.

What we geek out over in this episode: East Coast hip-hop group Mobb Deep, Prolific rapper Big Pun, Notorious B.I.G., Grandmaster Flash and the Furious Five, DMX, Pirates of Penzance, and South Pacific the Musical.

Bonus Material: The Hamilton Mixtape of selected songs and remakes from the musical featuring Kelly Clarkson, Sia, Miguel & Queen Latifah.

🔊Alexander Hamilton - Intro

Joe: Hello and Welcome to Riffs on Riffs, where we explore the collision of original and sampled tracks and the artists who made them. I’m your host, Joe Watson, and I’m here with my co-host, Toby Brazwell. What’s up Toby?

Toby: What’s going on Joe, glad to be here!

Joe: Together on this show, we’ll listen to legendary tracks and the timeless — but sometimes not-so-well- known — songs they sampled from. Today, we’re going to dive into a musical and cultural phenomenon, a show that takes a historical look at our forefather without a father, a man who wrote like he was running out of time, and someone who would have made a hell of an MC if he was around today. Toby, what’s his name, man?

Toby: Alexander Hamilton. His name is Alexander Hamilton…

Joe: That is beautiful my man, thank you. Today we’re going to break down some of the songs from the musical and listen to a few of the tracks that inspired Lin Manuel as he was writing. But first, let me ask you a question Toby. If you were going to debut a musical idea, what would be a few places you might do that?


Joe: Well, Lin Manuel had other ideas. Let’s rewind to May 12, 2009, and take a visit to Presiden’t Obama’s White House Poetry Jam…

🔊Poetry Jam

Joe: Started as concept album. Changed to musical, took about 6 years to complete, etc. Inspiration from Ron Chernow book In the Heights Broadway open August 6, 2015 What was your first exposure?

Toby: So back in 2007 there was a hip hop opera called Carmen that featured Beyonce, Mekhi Phifer and Mos Def. It was a hip hop opera and to my knowledge the first of its kind. I remember watching it and being enchanted with the artistry. The writing, and the guts to do it. Some of my friends will attest to the fact that I asked them if a hip hop opera would work on a larger scale. A lot of them said that it would come o corny and awkward…. that’s why I was so excited to see Lin Manuel do it. Listening to Lin Manuel do it was exciting because he was telling a story via hip hop but it was also good and paid homage to the greats in hip hop.

Joe: it also pays homage to well known founding fathers like Washington and Jefferson, and not quite as well known historical figures like Aaron Burr, John Laurens, Hercules Mulligan and Marquis de Lafayette. A er we’ve met some of these characters in the show, Hamilton steps to the forefront and proclaims his mission. Let’s listen to the song, “My Shot”.

🔊My Shot - Main

Toby: This song reminds me of the same feeling I got heard when I heard Eminem’s Lose Yourself. It was a song that spoke of rising up from where to attain greatness. My shot is very similar to Lose Yourself in feeling. It’s rally cry for one’s self con dence. Joe: It is all about empowerment and action — which of course stands in direct contrast to Burr’s “Wait for It”. The lyrics resonate with so many people, which is why you see t-shirts with “I’m just like my country, young scrappy and hungry”

Joe: Lin-Manuel packs multiple hip-hop references into this song. Let’s take a listen to the first one, where Hamilton talks about being 19…

🔊My Shot Nineteen

Joe: Toby, you recognized that reference right away. Tell me about it.

Toby: This is a direct shout out to Mobb Deep, from their 1996 track Shook Ones Pt II. Let’s have a listen…

🔊Shook Ones

Joe: The lyrics are almost identical. Hamilton had some serious hurdles to overcome as a child, and so did Prodigy from Mobb Deep, who had this to say about that particular line from Shook Ones: Prodigy quote: “What I meant was, all the stuff that I’d been through in my life – dealing with sickle cell and just dealing with life period. It forces you to grow up quickly. I was forced to deal with the pain and hanging in the streets, and wilding out. It makes you think like an adult and make adult decisions and be way more mature than your actual age. We’d been through so much. At 19, I felt like I was 40.”

Joe: Tell me a bit about Mobb Deep…

Toby: Mobb Deep gained their fame with their second album “The Infamous” released in 1993. This LP is one of my favorites and features plenty of my hip hop heroes. The first time I heard this was on a D Mixtape by DJ Dirty Harry from New York. I played that cassette till it almost popped in cassette player. Back in the day this was the only way that I go to get new music early.

Joe: You ever have any Big Pun on those mixtapes? He was a New Yorker…


Joe: Lin Manuel is a big fan of Big Pun. They share the same Puerto Rican heritage, and Lin has said that Big Pun was a master at “stacking internal rhymes into lyrics so densely and making them feel conversational”. That influence is very apparent. Let’s take a listen to how Lin Manuel stacks some internal rhymes in My Shot…

🔊My Shot - Big Pun Style

Toby: Lin Manuel definitely borrowed Big Pun’s alliteration and style for that rhyme. Let’s check out one of the best all-time examples of Big Pun’s ow, from the track “Twinz (Deep Cover ‘98)”


Toby: Big Pun- first latin rapper to go platinum. MTV has him listed as ranked at 22 of the 50 best MCs First time I heard him was on Fat Joe’s album entitled “Jealous Ones Envy” He was a stand out rapper and his album entitled Capital Punishment is hailed as a hip hop classic. In 1999 it was nominated a Grammy for the Best Rap album of the Year only to lose to Jay Z’s Hard Knocks life Vol 2. He did have major health issues- at age 18 he was 180 lbs, by the age of 21 he was 300 lbs. All of the health problems that came with this eventually led to his death in 2000 at the weight of 698 lbs. Big Pun Took the style that Kool G style was famous for and then ripped it- Many people tried to do this… but Big Pun did it the best.

Joe: Let’s listen to another example of Big Pun’s technical style with a song called Super Lyrical from his 1998 debut album, Capital Punishment…

🔊Super Lyrical

Joe: Big Pun is not the only New York connection to Hamilton. Lin Manuel was born in 1980 and grew up in New York, so it’s no surprise that he’s also clearly a fan of The Notorious B.I.G., a Brooklyn native. Lin pays homage to Biggie multiple times in the show, beginning with Hamilton spelling out his name for the audience…

🔊My Shot Alexander

Joe: Now let’s hear Biggie spell out his name on Going Back to Cali, from his 1997 album Life A er Death…

🔊Going Back to Cali

Toby: Those are clearly connected… Not the only example of how Lin pays homage to Biggie in Hamilton. Let’s listen to Cabinet Battle 2 from Hamilton…

🔊Cabinet Battle 2

Joe: I have to laugh at this one. I think Daveed Diggs is one of my favorites in the original cast — you can almost hear the twinkle in his eye, whether he’s playing Lafayette or Jefferson. This part of Cabinet Battle 2 references one of Biggie’s most well known songs, Juicy. I know we clean some of these songs up for the show, but suffice to say Biggie doesn’t say “Mr. President” in the album version of Juicy. Let’s have a listen to the sanitized version…


Joe: Juicy is a rags to riches chronicle of Biggie’s life, thematically aligns with Hamilton’s own rags to riches story.

Toby: …transition…

🔊Ten Duel Commandments

Joe: I guess if you’re gonna have duels, you gotta have rules…

Toby: * Duels were used back in the day to settle disputes * Willing to die to save face * Initially fought with swords, in later times guns were used So back to Hamilton… Lin used Notorious BIG’s song called the 10 Crack Commandments to illustrate the rules of dueling. Let’s take a listen to Biggie’s 10 Crack Commandments off of the 1997 release Life after Death.

🔊Ten Crack Commandments

Joe: Ironically, both men also died as a result of a “duel”. Sadly, the more things change…

Toby: … rap battles, diss tracks, etc. Hopefully now past point of killing for “honor”…

Joe: Hamilton would have been the king of the diss track, that’s for sure In the show, we see a couple of rap battles between Jefferson and Hamilton. Let’s listen in to Cabinet Battle 1

🔊Cabinet Battle 1

Joe: Lin Manuel is paying tribute here to rap pioneers Grandmaster Flash and the Furious Five and their iconic track, The Message…

🔊The Message

Joe: I love how a lot of these references are subtle — they are obvious to fans of hip hop, but they don’t beat you over the head and they are always in context and adding to the song. Here’s another example. You ever been in trouble?


Joe: Well, Hamilton is in trouble, and Washington wants to meet him inside…

🔊Meet Me Inside

Toby: I couldn’t help but smile, at this part in the play. It was so menacing- fueled by anger. The frustration that Hamilton was going thru at this point was tangible. For Alexander Hamilton to face off against Washington who was looked at like a GOD at this time showed just how much confidence he had in himself.

Joe: It’s interesting that you use the word menacing. Lin Manuel is a fan of DMX and his track, “Party Up in Here” — he liked the menace of a certain part of the song, and the foreboding of “what’s gonna happen outside?” Let’s listen…

🔊Party Up in Here

Toby: Do you remember that quote from Sting we talked about from an earlier episode? It had to deal with stealing?

Joe: Yeah I remember. Sting was paraphrasing TS Eliot “Immature poets imitate; mature poets steal; bad poets deface what they take, and good poets make it into something better, or at least something different.” ― T.S. Eliot, The Sacred Wood

Toby: To me borrowing and then making something completely new from it is the essence of sampling and a corner stone in hip hop. I think that’s exactly what Lin did with Hamilton and that outside of the historical accuracy, the musicality, the great songs, and the diversity and talent that he had on stage, makes this project more than memorable for me. And respected by hip hop purists. He borrowed some of the best elements of hiphop from our generation and then gave it in Hamilton.

Joe: Authentic and pure in shoutouts to musical theater, too. For example, there’s a line in Right Hand Man where Washington talks about being the model of a modern major general. Let’s listen…

🔊Right Hand Man

Joe: Turns out that’s a shoutout to as song called “Modern Major General” from the 1879 comic opera The Pirates of Penzance. “Modern Major General” is what they call a patter song. “The lyric of a patter song generally features tongue- twisting rhyming text, with alliterative words and other consonant or vowel sounds that are intended to be entertaining to listen to at rapid speed” — now what does that sound like?

Toby: Sounds like rap to me. Let’s hear it…

🔊Modern Major General

Joe: Here is yet another subtle nod to an iconic musical. In this verse from Hamilton’s “My Shot”, Leslie Odom Jr. as Aaron Burr mentions that “you have to be carefully taught”…

🔊My Shot Carefully Taught

Joe: This is a shoutout to the song “You’ve Got to Be Carefully Taught” from the 1949 Rodgers and Hammerstein musical South Pacific. Here is Matthew Morrison from the 2008 Broadway Cast…

🔊Carefully Taught

Discuss lyrical similarities (fear based in both cases)

Joe: We always like to end the show with some bonus material, and since Mr. Miranda is such a genius, he has this covered, too! Toby, you ever make a mixtape?


Joe: Well, Hamilton was originally going to be titled “The Hamilton Mixtape,” but was shortened. During the production of Hamilton, Lin-Manuel hinted that a mixtape of selected songs from the show was being recorded. That mixtape was officially released on Dec 2, 2016 and debuted at number one on the Billboard 200, selling 187,000 copies in the first week. 12 song cassette version made available in Feb 2017 The Hamilton Mixtape contains remakes and some deleted tracks from the musical.

Toby: There’s an insane list of talent on this mixtape. The Roots, Alicia Keys, Usher, Nas, Busta Rhymes, Jill Scott, Andra Day, Kelly Clakrson, Sia, Queen Latifah — too many to mention…

Joe: You are correct, and it’s also insane to think we could do The Hamilton Mixtape justice in a few short minutes, but let’s take a listen to a few of the tracks… The first single released was Kelly Clarkson’s remake of “It’s Quiet Uptown”. I remember hearing this on the radio long before I had ever heard the soundtrack, and as always being in awe of Kelly’s voice…

🔊It’s Quiet Uptown

Joe: The song Satisfied is one of my favorites from Hamilton — lyrically, thematically, musically. I didn’t think anything on The Hamilton Mixtape could hold up to Renée Elise Goldsberry’s fantastic voice. Then, I saw they gave “Satisfied” to Sia, and I knew all was right in the world. Huge Sia fan since I heard Zero 7’s Simple Things, an album that is a default happy place. Sia is one of those “damn, now I have to share” artists. Toby, you have those?

Toby: … Anyway, this is what Lin Manuel had to say about Sia…

🔊Weaponized Vowels

And if Sia was not enough, “Satisfied” also features Miguel as Hamilton, and the queen herself, Queen Latifah. Let’s settle in for about 30 seconds and hear how it all comes together…

🔊Satisfied - Hamilton Mixtape

Toby: Well, that’s it for this episode, and that’s it for Season 1 of Riffs on Riffs. We hope you have enjoyed exploring the songs that inspired Hamilton…

Joe: I know we will never be satisfied until we are back again with another season of Riffs on Riffs. In the meantime, we’ll take you out with a Hamildrop — Lin Manuel’s monthly release of The Hamilton Mixtape, Volume 2. This is another track from rap pioneers Mobb Deep, one of the last recordings completed before Prodigy’s death in June of 2017. Have a listen to “Boom Goes the Cannon”, and we’ll catch you next season.

🔊Boom Goes the Cannon

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