Anthony Ramos’ Long Journey to ‘In the Heights’ – The Hollywood Reporter

The first time Anthony Ramos auditioned for In the Heights was exactly a decade ago. He was 19 and trying out for an ensemble part in a nonunion national tour of Lin-Manuel Miranda and Quiara Alegría Hudes’ musical about dreaming, striving and surviving in New York City’s Washington Heights neighborhood; he made it four rounds and danced for Miranda in the final audition but didn’t make the cut.

Miranda has no memory of this first encounter, not that he would be expected to: In 2011, Ramos was just another drama school graduate amid a sea of chorus line hopefuls trying to get a gig — a hard enough task already but made even more difficult in an industry where Latino roles were scarce.

He would try out once again for another Heights show, and then a third time: On that attempt, it was a regional theater production for Actors’ Equity members, and although he didn’t belong to the union, he followed the casting director into an elevator at Chelsea Studios and slipped him his headshot, securing a last-minute audition to perform a song and recite three lines of dialogue. The casting director liked his rendition of Bruno Mars’ “Grenade” enough to send him back out into the hallway with 10 pages of dialogue and music from the show. Fortunately, Ramos was prepared: As the one musical to feature a Latino company, “[Heights] was the only show I felt like I could have a part in, so I had already learned all the male parts.”

He ultimately landed a major supporting role: Sonny, the protagonist’s younger cousin — as well as his coveted union card. That made him eligible, two years later, to try out for another project, an off-Broadway production then called The Hamilton Mixtape. This time, Miranda remembered him.

“He sang ‘My Shot’ like he was Alexander Hamilton reincarnated and, if given a chance, he would run the world,” Miranda says. “I’ve never seen a hungrier presence. He has that thing that movie stars have, which is, the moment you see them, you are rooting for them to win.”

That’s what Warner Bros. is banking on when the latest version of In the Heights that Anthony Ramos has gone after (this time quite successfully) opens in theaters and on HBO Max on June 11. Now he’s the lead — Usnavi, the bodega owner working to save up enough money to move to his parents’ Dominican Republic homeland — in the highest-profile, highest-pressure role of his career.

“Besides the regular assets of a leading man, our movie is unique in that this person had to be able to cross mediums,” says director Jon M. Chu, who compares Ramos to a multihyphenate talent on the order of a young Will Smith. “He had to be able to act through singing, and dance through dialogue. He had to rap from that genuine center of truth and bring moments as small as the flicker of an eyelid to a big number where he’s moving just as well as the best dancers in the world. And then there’s the English and Spanish on top of that. As soon as Anthony got on camera, it was very clear to me that this guy was a star for a whole generation of people.”

But the $55 million movie adaptation of Miranda’s first Broadway musical won’t just test Ramos’ star power. It will also help gauge the industry’s health, being among the first wave of summer films to hit theaters during their post-COVID reopenings (its release was pushed from June 2020) while also part of WarnerMedia’s controversial same-day streaming debut on HBO Max. In success, the movie has a chance to become a cinematic cultural touchstone that Latinos, who over-index as moviegoers but are the most disproportionately underrepresented demographic in Hollywood, have been waiting for.

“We haven’t had a movie that feels like Black Panther or Crazy Rich Asians,” says Ramos, who on the Heights set was prone to kick off each day with the rallying cry, “For the culture!” or its variants, “For la raza!” and, “For my familia!”

It was raining and overcast when the ensemble shot one of its massive showstopping numbers, “96,000,” which in a departure from the stage version, is set at the neighborhood’s Highbridge Pool. “Everybody was in that water freezing, and it was like, ‘Yo, remember: It’s for the culture,’ ” Ramos recalls. “We’re yelling out, ‘This is for the motherfucking culture!’ You could just feel the ancestors, years of people who feel like they have not had this chance, understanding that this moment is our chance. That’s what I kept in my heart every single day when I went to set.”

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Ramos’ favorite In the Heights lyric is Usnavi’s epiphany in the closing number, fittingly titled “Finale.” Two years after production wrapped and over Zoom from his temporary quarters in Montreal (where he’s shooting a Transformers movie), he smoothly raps 16 bars, which end on the words “I’m home.”

“That is what sums up In the Heights,” says Ramos, but it’s also what sums up his own 29 years on the planet. “I grew up in New York, and my dream was to not live there. Figuratively and physically, New York has done a number on my ass. I know what it’s like to struggle, to walk eight blocks in the cold to your apartment. I know how it feels to be hungry for my dreams and also hungry like, ‘I could use some McDonald’s right now.’ “

Ramos grew up in project housing in Bushwick, Brooklyn. His father wasn’t around, and his mother worked as a medical biller to support him and his two siblings. “She was making $30,000 a year before taxes, so that was barely 10 Gs a kid,” he recalls. “Contesting with poverty and always seeing her stressed was hard, and there were drugs and alcohol in my family — that was hard to deal with as well. I just didn’t want to be in that situation anymore.”

As a child, Ramos found emotional escape in baseball and music, buying bootleg CDs — Eminem and 50 Cent but also salsa artist Héctor Lavoe — for $5 a pop from a vendor three blocks from his family’s apartment. “I feel bad for not paying for an album at the regular price as a kid, but anywhere between $12 and $20 was a lot of money. Five dollars I could get,” he says. “And this dude always had good bootlegs. You knew that he was going to have all the songs, none of them were going to skip, you were legit going to get your money’s worth.”

When he was 12, Ramos moved out of his mother’s house and in with his aunt in southwest Brooklyn. There, when he wasn’t sleeping on a leaky air mattress (later upgraded to a $60 roll-out bed) in the room he shared with his two cousins, the three boys would stay up late writing and recording songs using Windows Media Player and a voice memo app. Other than a musical trio he formed in eighth grade to sing Temptations songs at school assemblies, that was the extent of Ramos’ pursuits as a performer. He focused on baseball for the next couple of years (he was a two-year starter and earned the team’s highest batting average one season) until 11th grade, when he heard an announcement over the PA system calling for auditions for a program called Sing. Ramos, thinking he was trying out for a talent show, sang John Legend’s “Ordinary People.” But it was a musical — worse, a student-created, Greek-mythology-themed jukebox musical — and, to his compounded horror, he landed a lead, which he reluctantly accepted after some coaxing from his high school’s musical theater director, Sara Steinweiss.

“I’m wearing this ridiculous crown, I look like Burger King, I was wearing eyeliner, there was way too much blush on my face,” he says. He remembers crooning an altered version of “Baby, It’s Cold Outside” to his scene partner onstage. “It didn’t matter how ridiculous I may have thought I looked before we started. It didn’t matter any of the things that might have made me insecure about what I was doing, because it was just this moment where I felt the energy of the audience and I’m singing to her and singing out to the audience and I was like, ‘This feels amazing.’ “

Ramos continued to chase that feeling for the remainder of high school, juggling baseball with musicals. He hoped to go on to SUNY Purchase, which had both a baseball and a theater program, but amid continued instability at home (he couch-surfed throughout his senior year), he failed to submit his financial-aid paperwork in time and all his college applications were withdrawn. Ramos, sick of staying poor, was ready to give up and join the Navy, but Steinweiss encouraged him to apply to the American Musical and Dramatic Academy, sitting him down to write the essays together and even paying the $50 application fee and submitting the package herself.

“I knew that if I didn’t do this, he wasn’t doing it,” says Steinweiss, whom Ramos now calls a mentor and close friend. “It’s not because he was lazy but because he was exhausted from life.”

Ramos got into AMDA (he auditioned with a King Lear monologue) but couldn’t afford the conservatory’s tuition, so Steinweiss arranged for him to meet with a scholarship program funded by the Jerry Seinfeld Family Foundation. Although his academics weren’t up to the par of the typical recipient’s, they offered to pay the full ride.

“That was when my life changed in an instant,” Ramos says. Steinweiss agrees: “The minute that happened, I knew all bets were off for this kid.”

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It didn’t take long for Ramos to realize that he had plenty to learn to catch up to the experience and institutional knowledge of his lifelong-theater-kid classmates: “They knew Rodgers and Hammerstein, Stephen Sondheim, Andrew Lloyd Webber. I didn’t know shit about theater.” Ramos was determined to get into AMDA’s dance workshop, so he worked the desk at the Roy Arias Dance Studio in midtown Manhattan in exchange for $3 classes: “If I could get nice with the dancing, then it just gives me another opportunity to get a job.”

There were other strategies to boost his odds. “Folks would say to me that if you grow your hair out and speak in American Standard, you can be more ethnically ambiguous; you won’t be in the ‘Latino box.’ I thought that shit was a box, as opposed to being a superpower and just who I am,” says the actor, who years later would be seen on the Grammys stage brandishing the Puerto Rican flag in glee when the Hamilton cast won best musical theater album. “I believed that [box] shit for a little bit, but I don’t want to be hired for being ambiguous. I want to be hired for who the fuck I am.”

Still, Ramos was having trouble booking work, so he was in low spirits by the time he finally got to catch In the Heights during his final semester at AMDA in 2011, while the show was in its closing weeks on Broadway. Seeing the Latino cast onstage gave him enough motivation not to quit, even though the ensuing year was rough, with long gaps between tough gigs: local shows that were constantly late on payment, nonunion national tours, cruise ship performances.

Landing Hamilton, in which he played the dual roles of Hamilton’s son and one of his allies, was a game-changer, and it might seem like a given that Ramos would go on to headline the Heights movie. But Chu initially wanted a slate of unknowns and was conducting a massive casting search in 2018. Miranda had seen Ramos play Usnavi for an abbreviated staging of the musical at the Kennedy Center that spring and urged Chu to take a meeting with him.

“It fits him better [than me]. He doesn’t have to put anything on,” says Miranda of Ramos’ take on the character that Miranda himself originated onstage. “I think spiritually I’m closer to a Nina [the barrio’s burdened overachiever in Heights] than an Usnavi, and watching him embody the hopes and struggles of this neighborhood just felt like a suit that fit him perfectly.”

Over breakfast at Toast in West Hollywood, Ramos and Chu formed an emotional connection instantly. “We just wept together, two grown men over coffee crying about his story, my story, and where we were in the world,” the director says. “He embodied everything about this new Usnavi. There was so much heart and so much love pouring out of his pores, he was like speaking poetry at the table. You look at his face and it just expresses his whole journey.”

As befitting a classic movie musical, In the Heights opens with a grand number in which the camera sweeps through the neighborhood, winding through small businesses and apartments before catching up with the full company at the climax, salsa-stepping their hearts out on Audubon Avenue.

“Usually in a musical you pull back, but this one was a call on the fly,” says Chu, who recalls looking up at the rapidly sinking sun and determining they had two takes left to run through the complicated sequence. “What if I pushed in? Amongst all these people, we’re going to find our main character, surrounded by the best dancers in the world doing very, very fast salsa moves, and he’s dancing as big and as precise as everyone else, and we’re going to tell his story. [Anthony’s] focus right into the lens on those two takes we had left is so intense, he’s the glue that keeps it all together.”

For his part, Ramos says the support of the cast and crew kept him from feeling the pressures of his transition from stage sidekick to cinematic leading man.

“I think he knew his responsibility and the weight of this part and this movie,” says Olga Merediz, who has played Abuela Claudia, the barrio’s spiritual grandmother, opposite every version of Usnavi on- and off-Broadway and now onscreen. “Yet the way he carries himself, he’s very sure of himself. He’s got this sexy charm, he knows he’s talented, and he’s got this relaxed Latino kind of confidence.”

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“Music’s always been my first love,” says Ramos, adding that after leaving Hamilton in early 2016, he took a three-month acting hiatus to hole up in Los Angeles with his music producer, Will Wells, to write songs. The two met during Hamilton‘s off-Broadway run, where Wells was the production’s electronic music producer: “Every day during the show, every time Anthony got up to sing ‘Raise a glass to freedom,’ my ears would perk up. I just believed him,” Wells says. “After opening night I went up to him and said, ‘Everybody up there is obviously brilliant, but you’ve got something special. Have you ever made a record?’ “

In 2018, Ramos independently released an EP, The Freedom, and for the next couple of years established a routine: “God willing, get some money from movies and TV shows [which have included A Star Is Born, Godzilla: King of the Monsters and Netflix’s She’s Gotta Have It series], and then spend the money on [making] music.” Now he’s more adept at multitasking, working on songs during downtime on location. “Anthony goes everywhere with a mini-rig and microphone,” says Wendy Goldstein, president of West Coast creative at Republic Records, which signed him in 2019. Goldstein believes conditions are better than ever for a multihyphenate like Ramos to succeed at the box office and on the charts. “He gets more done than some of my artists that just have one job.”

Republic released Ramos’ debut album, The Good & the Bad, in the fall of 2019. It’s an autobiography that hops through multiple musical genres as it winds through his adolescent angst and romantic escapades, including three tracks about his relationship with fiancee Jasmine Cephas Jones. The Hamilton alums, who were engaged on Christmas Eve of 2018 and have not yet set a wedding date, are firm about maintaining boundaries between their personal life and professional obligations, so those seeking insights into their bond will have to look for clues in “One More Hour,” “Isabella” and “Mind Over Matter” (the couple offer a tantalizing glimpse into the chemistry of their six-year relationship in the music video for the latter).

The Good & the Bad performed modestly, debuting on top of iTunes’ pop albums chart and peaking at No. 21 on Billboard’s Heatseekers chart, but Ramos and Republic have pop star ambitions for follow-up Love and Lies when it drops this summer. While his first two albums explored heavier subjects including politics and nostalgia, the new material is “12 bangers,” Ramos says with a laugh, perhaps accurately gauging the soon-to-be post-pandemic mood. “People don’t want to be in their feelings, they want to be getting lit!”

Love and Lies‘ lusty focus is part of a new phase for Ramos, who in addition to bringing a more youthful sex appeal to Heights‘ Usnavi, also stars alongside Megan Thee Stallion and Euphoria‘s Jacob Elordi in Calvin Klein’s Spring 2021 underwear campaign, shot by Terence Nance. It’s a far cry from portraying Alexander Hamilton’s precocious young son on Broadway, where in many ways Ramos came of age.

“Hamilton was like a crash course for all of us,” says Miranda. “When Anthony came in, he was just geeked to be there, and I think he came out as someone who could credibly lead a company on his own with grace and maturity and the understanding that the person at the top of the call sheet determines the tone.”

The boy who couldn’t wait to move out at 12 now finds ways to keep his family close when his skyrocketing career takes him away from his New York City home base. Ramos’ mother and sister both have cameos in Heights, while his brother travels with him as his right-hand man for all his big projects, which in 2020 included shooting the upcoming Amblin sci-fi feature Distant in Budapest and the new pandemic-set season of HBO’s In Treatment, which premiered May 23. In the therapy drama, Ramos plays new patient Eladio, a home health aide haunted by insomnia and his childhood of parental abandonment, and he says the role — and being in therapy himself — has helped him find healing for his family’s turbulent past and grounding for his restlessness.

“It took me until adulthood to appreciate New York,” says Ramos, conjuring up the memory of yet another grueling Heights sequence, this one for the sweat-soaked “Carnaval del Barrio” number that takes place when the residents decide to throw a spontaneous block party in the back alleys during a prolonged summer blackout.

“At the end of that shoot, everybody was so hyped that we all huddled in a circle cheering, ‘New Yorrrrk! New Yorrrrk!’ ” he recalls. “It was just this New York resilient moment we had together singing this song about pride: alza la bandera, raise the Puerto Rican flag, the Dominican flag, the Mexican, Cuban flag. Pa’rriba esa bandera, alzala donde quiera! Raise that flag wherever you want. Until the day I die, I’m going to be proud of where I’m from. That was the shit. Some of the days were hard, but every day was more than worth it.”

This story first appeared in the May 26 issue of The Hollywood Reporter magazine. Click here to subscribe.