Making The Hamilton Mixtape: Lin-Manuel Miranda explains the stories behind the songs

The Hamilton Mixtape has gone through a handful of incarnations: Lin-Manuel Miranda conceived of Hamilton as a mixtape of songs about Alexander Hamilton’s life before he gave any thought to writing it as a Broadway show. “I was going to write a concept album called The Hamilton Mixtape, wherein I would write some songs that were like highlights of Hamilton’s life, a la Jesus Christ Superstar or Evita, and then someone would figure out how to stage it later,” he tells EW. Then he did write it as a show himself, but kept “Mixtape” in the title — until about a year before Hamilton opened off-Broadway at the Public Theater in Manhattan.

As it played at The Public, Miranda thought about making Mixtape happen again, closer to its current form, with different artists covering the show’s songs. But that didn’t make sense if the rest of the world hadn’t yet heard those songs. So finally, after Hamilton opened on Broadway, snagged a Pulitzer, Grammy, 11 Tonys, and took over the pop culture universe, the Mixtape began coming together once and for all: A brilliant pop revision of the smash musical, with A-list artists and lesser known rising stars all taking part.

Below, Miranda and collaborators like The Roots’s Ahmir “Questlove” Thompson, Kelly Clarkson, Wiz Khalifa, and more share the stories behind their songs. The Hamilton Mixtape is out Dec. 2.

“Wrote My Way Out” by Nas, Dave East, Lin-Manuel Miranda, Aloe Blacc

When work started on The Hamilton Mixtape, show creator Miranda had one rule: None of the play’s original cast members would be involved so as not to show favoritism among them. But he soon changed course. “I heard that beat, and I heard Nas’s verse, and I had some s— to say and I broke my own rule,” says Miranda, 36. “I felt like, if I’m going to put my two cents anywhere, that would be the place to do it.” Miranda rhymes about schoolyard bullies beating him up for reading, which made his mother cry when she heard it: “I’m talking about stuff that happened when I was very young. It really hit her hard,” he says.

“Wait For It” by Usher

While most of the album’s guest stars were given creative freedom, Miranda admits he was protective of this track, one of the musical’s highlights, which is sung on stage by the Aaron Burr character. “I may never write a song that good again,” he says. “That’s the one I was pickiest about, because those arpeggios and the dancehall rhythm make the song what it is.” Finding a singer who could keep the tension between the melody and rhythm was crucial. “Usher’s vocals are just incredible,” Miranda says. “He really makes the song his own.”

“An Open Letter (Interlude)” by Watsky featuring Shockwave

Watsky, famous on YouTube for his lightning-speed rapping, is a friend of Miranda’s. “I actually wrote a soliloquy that I had Watsky in my head for of a drummer boy on the front line of Yorktown,” he says. While he might resurrect that piece for The Hamilton Mixtape Vol. 2, Miranda was thrilled to have Watsky, with “his ability to sort of triple-time and do these incredible lyrical runs,” record this discarded rap of Alexander Hamilton’s insults to President John Adams.

“Satisfied” by Sia featuring Miguel & Queen Latifah

Miranda was a fan of Queen Latifah growing up, and admits the character of Angelica Schuyler was inspired by the hip-hop queen. So when Miranda met Latifah after a performance of the musical, he seized the opportunity to get her on board for Schuyler’s scene-stealing raps. (Sia contributes the character’s sung parts.) “I said [to Latifah], ‘You are one of my favorite MCs, full stop. Angelica exists because you were a voice in my ear growing up,’” Miranda recalls. “I wanted to hear her rapping again so badly!”

“Dear Theodosia” Regina Spektor featuring Ben Folds and “Dear Theodosia (Reprise)” Chance the Rapper feat. Francis and the Lights

Hamilton and Burr’s lullaby to their newborn children was in high demand: Both Regina Spektor and Chance the Rapper, a new father, requested to cover it. “We were like, ‘Okay, who’s gonna be the bad guy to tell this person that the other one has the song?’” producer Ahmir “Questlove” Thompson recalls. But when both artists submitted remarkably distinct tracks, the team made an unorthodox choice. “I said, ‘Well, this is a mixtape. There isn’t a rule against what we can do with it,’” says Thompson. “We decided to keep both.”

Ben Folds, for his part, is pleased with that decision: “Reggie sang the s— out of that song,” he says. “I was just happy to be there. I would have been the water boy if she wanted me to… But I was glad I didn’t have rap.”

“Valley Forge (Demo)” by Lin-Manuel Miranda

“One of the things we always talked about with the Mixtape was giving people glimpses of songs that didn’t make the cut,” Miranda explains. One such demo is “Valley Forge,” a haunting song about the long winter Washington’s army spent in 1777-8. “That was a demo I was always really proud of,” he says, “But it isn’t dramatically interesting to watch a bunch of people freezing to death slowly. I took the best lines from it and put them in a different song called ‘Stay Alive.’” Still, it’s a fascinating—if morose—track on the Mixtape, and also showcases Miranda’s voice in a new way: “All those ‘Ooh, ooh, ooh’s’ are all me. Everything on that track is my voice. It’s me getting my Bobby McFerrin on!”

“It’s Quiet Uptown” by Kelly Clarkson

The pop star admits she didn’t know what she was getting into when she agreed to “modernize” one of the musical’s most wrenching ballads, which follows Alexander Hamilton and his wife Eliza as they struggle with life after their teenage son’s death. Clarkson says Hamilton mania hadn’t hit her hometown of Nashville when Atlantic Records chairman and CEO Craig Kallman sent her the song early one morning. She was shocked at its gravity: “I sent an email back to him with a lot of expletives,” she recalls. “I was so angry, because I was pregnant with my son, and it’s all about their son dying. I was a complete mess, but I was like, ‘It’s beautiful. I’ll try and do it, but I can’t promise you I can get through the dang thing.’” In the end, Clarkson triumphed, but she says, “It was literally the hardest thing I’ve ever done in the studio!”

“That Would Be Enough” by Alicia Keys

Miranda says his favorite evening during the making of Mixtape started with a phone call. “We got a call from Alicia Keys, who had agreed to do ‘That Would Be Enough,’ saying, ‘She doesn’t want to just send it to you, she wants to play it for you in her studio and talk to you about it,’” Miranda recalls. “I turned to Jonathan Groff [who originated the role of King George on Broadway], who was my roommate at the time, and said, ‘Do you want to come listen to Alicia Keys’s version of the song with me?’” He breaks into excited giggles at the memory. “So we jumped in a car immediately after our show, raced to her studio downtown, and as the Great Blizzard of 2016 started, we were sitting in a room at midnight with Alicia Keys—not only hearing her amazing version of ‘That Would Be Enough,’ but she also played us half the tracks on her new album early.”

“Immigrants (We Get The Job Done)” by K’naan, Snow Tha Product, Riz MC, Residente

This entirely new song—inspired by the musical’s showstopping line of dialogue, “Immigrants, we get the job done!”—was borne out of a conversation between Miranda and Atlantic’s VP of A&R Riggs Morales. “Riggs and I are both Latino,” Miranda says, “and we were like, it would be amazing to find a way to get Residente—maybe the most famous Spanish language rapper—on this mixtape.” (He also happens to be Miranda’s third cousin). “I said, ‘What if we do something around [that dialogue]?’ It’s such a highlight of our show. It gets a response every time from the audience.” The pro-immigrant message is increasingly relevant postelection. “It has become more potent,” K’naan says. “It’s more of a fight song.” Adds the Mexican-American hip-hop artist Snow Tha Product: “Now more than ever, we need to speak on these issues.”

“You’ll Be Back” by Jimmy Fallon & The Roots

Of course, there are lighter moments—like Jimmy Fallon’s cover of King George’s Brit-pop inspired breakup song, which fulfilled a dream for Thompson as a musician and producer. “I got my fantasy of going full vintage,” he says. “I’ll put it this way: Half of the Beatles’ catalog is part blues, part Chuck Berry rock-n-roll, and a lot of Tin Pan Alley, Gershwin-era Broadway stuff. My albums don’t personally give me the space to do my version of ‘Getting Better.’ So this allowed me at least a four-minute moment to say ‘What would Ringo do? What would George Martin do?’ That was probably the most fun we had.”

“Helpless” by Ashanti featuring Ja Rule

“Ashanti and Ja Rule were in my head when I was writing ‘Helpless,’” Miranda says. “It has the structure of an Ashanti-Ja Rule song: two verses, two choruses, a guest rap feature, then back to the chorus and around.” Thompson knew “Helpless” was based on one of their late ‘90s, early-aughts duets, too, and it didn’t make sense to him that the team would consider anyone else for the job. “When it came down to figuring out these songs [on the Mixtape], I was just like, ‘Dude, this is the white elephant in the room: Are you guys really not gonna go after Ja Rule and Ashanti?’” he recalls. “’You wrote it for them. You might as well just have them do it.’” When they agreed, Thompson says, “I was happy as hell.”

“Say Yes To This” by Jill Scott

Scott turned “Say No To This”—in which a married Hamilton succumbs to seductress Maria Reynolds’ temptations—into a role-reversing song. “I didn’t struggle with it at all,” the R&B singer says of writing the seduction from Maria’s point of view. “It kind of flew out because the music is so good—it takes you on a journey by itself. When I listened to it, it seemed a little slinky. It seemed aggressive and sexy and strong. [Maria] is not a loser. She’s offering him the best thing he’ll ever get in life!”

“Congratulations” by Dessa

Miranda says it was a “no-brainer” to ask Doomtree singer/rapper Dessa to take on Angelica Schuyler’s bold dismissal of Hamilton after he cheats on his wife, Angelica’s sister Eliza. “She has the Angelica skillset: She’s an incredible singer and an incredible rapper,” Miranda says. “Congratulations,” which was part of the musical’s off-Broadway run but was cut for Broadway, “has both those things in equal measure.”

“Burn” by Andra Day

Scheduling issues have kept R&B star Andra Day from catching Hamilton on Broadway (“I’m the only person on the planet who hasn’t seen it,” she says), but she was deeply familiar with the story. “I was actually obsessed with Alexander Hamilton in school,” she says. She chose to cover “Burn” after being drawn to Eliza’s “raw, fiery, painful emotion,” and says it was easy getting into the mindset of Hamilton’s wife when she finds out her husband has had an affair: “I already had such an empathy for her. Even before the show came out, I was like, ‘You know what? The guy’s a dirtbag.’”

“Cabinet Battle 3 (Demo)” by Lin-Manuel Miranda

Hamilton fans have been eager to hear this early demo since its lyrics were published in Miranda and Jeremy McCarter’s coffee-table book, Hamilton: The Revolution, this past April. “I totally wrestled with this rap battle and spent months writing it,” Miranda says. “We did it in one workshop, but you just get to a point where you look at all these flawed, human characters, and they didn’t do anything. Nothing really happened on slavery until the Civil War a hundred years later.” They couldn’t justify spending six minutes on a song where nothing changes by the end, so “Cabinet Battle 3” never made it into the musical. “But it was worthy for me to write, and cathartic for me to write, so I’m glad it’s included,” Miranda says.

“Washingtons By Your Side” by Wiz Khalifa

While Wiz Khalifa admits that “Dear Theodosia” made him cry when he saw Hamilton, there was only one song he instantly felt he could rework and make his own: Thomas Jefferson and Aaron Burr’s taunting, “Washington On Your Side.” “I was like, ‘That’s the one,’” he says. Miranda adds, “He was like, ‘I want to do Washington’s On Your Side,’ but I want to be talking about money,’ and we’re like, ‘Go! Go and bring it back!’” The result was a hit with Miranda: “I was just happy he liked the idea,” says Khalifa, “instead of thinking it was kind of weird.”

“History Has Its Eyes On You” by John Legend

When Miranda was devising Hamilton’s version of George Washington, one of the artists he drew inspiration from was John Legend—so it was only natural to ask Legend to cover one of Washington’s most powerful numbers on the Mixtape. “We had a quick phone conversation, and then he brought us back this beautiful, gospel-inspired remix of it,” Miranda says. Thompson was also floored by Legend’s take on the song, and it broadened his own vision of what the Mixtape could be. “That totally blew me away,” he says. “That was one of my jaw-drop moments, like, ‘We can go off-script and make this a gospel song?’ That’s when I realized, ‘This can go anywhere.’”

“Who Tells Your Story” by The Roots featuring Common & Ingrid Michaelson

Common was another one of Miranda’s inspirations for the George Washington character: “He’s got Washington-level moral authority,” Miranda says. So the significance of one of his idols contributing a verse to this reimagining of the musical’s final number was not lost on him. “To hear him reference lyrical moments [from the show] in his verses that he wrote—‘I write hard rhymes like I’m runnin’ out of time’—that’s thrilling to me, as a lifelong Common fan,” Miranda says. “It gets very dusty in the room if I talk about it.”