How her Tiny Desk Contest win returned Alisa Amador to a life in music

In 2018, Alisa Amador submitted a video to NPR’s Tiny Desk Contest for the first time. She performed the song, called “Talkin’,” in front of a classroom whiteboard, electric guitar slung over her shoulder, flanked by a drummer and a bassist. Upbeat and witty, “Talkin’” paired wry lyrics about dating in the social media age with a swingy hook and, most notably, Amador’s powerful voice. It was clear from the young singer’s deft musicianship that she was an artist to watch.

And watch her we did. 2018 happened to be the first year I convened a panel of musicians and journalists to anoint a local Tiny Desk Contest favorite on behalf of WBUR. Amador’s was one of the first of more than a hundred Massachusetts entries that I pored over, and it stuck with me. The next year, Amador submitted again — this time, with an acoustic guitar, backed by a standup bass. Her entries since then have tended to be quiet and introspective, her lyricism subtle. These songs are less showy than “Talkin',” but arguably more skillful. Amador was always a top contender among the panelists when we sat down to choose a local favorite. Maybe, I thought, this year would be her year.

It turned out the judges at NPR Music agreed. Amador is this year’s Tiny Desk Contest winner -- for the whole country, not just Massachusetts. She won with a song that we premiered on WBUR at the end of 2020, called “Milonga Accidental.” It is the first Spanish language song Amador ever submitted to the contest.

Amador grew up in a bilingual household in Cambridge. Her parents, Rosi and Brian Amador, front the long-running Latin folk band Sol y Canto, which draws on the family’s roots in Puerto Rico, Argentina and New Mexico, as well as their connection to the Boston folk music scene. For their daughter, music is both a birthright and a source of ambivalence. “Milonga Accidental” explores the feelings of not-belonging produced by Amador's cross-cultural identity. She sings directly into the camera, voice low, strumming a quiet, yet insistent, rhythm on her electric guitar. Though she provides an English translation to the lyrics in the video's description, the song's meaning comes across through a melody that's as yearning and curious as its words.

I caught up with Amador over Zoom the day after the announcement. The win, she told me, came as a shock — not least because she had recently decided to quit pursuing a career in music, an endeavor she described as “wrought with despair.” In our conversation, which has been edited for length and clarity, we talked about Amador’s love for the Boston folk music scene, how she found community through the Tiny Desk Contest, and what it means to belong.

Amelia Mason: I've been hoping for a Boston or Massachusetts artist to win Tiny Desk for years, so thank you for making my dream come true!

Alisa Amador: [laughs] Thank you! I’m honored.

How long have you been sitting on this info? They must have told you a while ago.

The hardest secret I've ever kept, yeah. I was told on Thursday evening and the news came out on Tuesday, so there really wasn't that much time and it's been a really quick turnaround.

I was actually really scared when I first got the news. Like, honored and amazed, but really scared. 'Cause, especially having just been in the process of stepping away from music, to suddenly be thrown into a national spotlight is, like, a total 180. It's just new to me. I don't know. I've never had this much attention at once. 

So I was just scared. And then as we prepared for the announcement, I did a lot of soul-searching and journaling and asking myself, “Can I do this? Is this what I want to do?” And, yes, it is. It also just feels like I'm compelled to do this. It feels like this is what I am meant to do, as cheesy as that sounds.

So many people enter the contest. You've done it consistently for, like, five years, which they keep bringing up. Like, "Wow, she sure is a go-getter!" 

Well, the thing about entering the contest for me is that it was never about winning, ever. It was about being part of a community. Through the contest, and then through your work with WBUR featuring the Massachusetts entries, I've made some of the greatest friends and colleagues of my life.

Oh, really? Who?

Hayley Sabella, Kaiti Jones. Those are two of my closest friends. And we've played together, toured together, written together. These are people who have made me who I am, thanks to the Tiny Desk Contest. … "Contest" feels like a funny word when it really feels so much more about music community, and building community, and connecting people with each other and inspiring each other and reminding each other that we exist during this pandemic.

I've been watching you enter for years, and I actually very distinctly remember the first entry that I saw of yours, which may have been your actual first entry. 

Yeah, with the band.

Over the years, you really pivoted in terms of the kind of stuff you were submitting. You still make that music that is more upbeat, and a little jazzy, and with the big voice. But everything you've entered with since then has been much more intimate. I wondered if you could talk about that sort of evolution. 

Every year I shared a song that felt like it was timely and felt like that was the moment to share it. And it's especially been the case during the pandemic that I was alone in my room. I didn't need to play with an amplifier anymore. [laughs] So I started playing acoustically way more, and writing acoustically. And so since then, my submissions have been acoustic, solo and dealing with painful, vulnerable themes.

But something that I want to emphasize is that my music is about holding all of these experiences that can feel contradictory in the same space. And how lived experience has all of that. So my music is funky and rocky and jazzy, and then it's also quiet and introspective. And it's also in English, and it's also in Spanish. It's also joyful and it's also heartwrenching. And all of those things can be true. All of those things are a part of all of us. So, it just feels really affirming that I won with a song in Spanish that is introspective. But I also sent in songs that cover that entire range. When I got the call that I had won, the first thing that Bob Boilen told me, after he said that I won, is that the NPR Tiny Desk team has loved every single one of my songs. And I think that that felt even more poignant to me than anything. To feel like, “We've loved every version of you.”

… And then “Milonga Accidental,” which is a song about multiplicity, a song about feeling like you're fractured and like you don't fit into any identity, like you're constantly contradicting yourself — that's what this song is about. The chorus is this question: “When will I know how to decipher my purpose? When will I feel at home in my voice?” That feels so crazy to me, that I asked that question, and the answer was, "You win! This is an American story that needs to be heard more loudly across the country.” I've been hiding that truth about myself for so long. And to share it, and then be uplifted like this, is so poignant to me. 

Can you say more about hiding that side [of yourself]? What do you mean?

Yeah. I think I used to worry that my music in Spanish wouldn't be well-received or that people would get confused. … And that singing in Spanish and using folk rhythms from the Spanish-speaking world would just complicate things more for me in terms of description, in terms of audience and attendance and how to promote myself and whatever. I'm realizing that that was my own internalized s---. That was my own internalized fear around difference. 

I think of you as being, in a lot of ways, a product of the New England folk scene. But also, you're not typical in other ways. It's an English-speaking scene, it's very white. … How do you feel like that scene shaped you, and do you feel a sense of belonging in it? 

I'm still very much living in that world, so it's like asking a fish about the water that they swim in. But I feel so lucky to live in a city that has such a robust songwriting community and so many musicians moving through it. … They're not necessarily going to stay, but they pass through that space. And then there are the songwriters and the musicians who choose to stay, like my family. Latin folk musicians! Who would've thunk that Boston would be the good place for them to be based? But that's how it shook out.

There's just so many different kinds of music, actually, in the Boston scene, if you know where to look. …But the songwriter scene is definitely where I've been most, especially in my adult life, I've been kind of enveloped into that community. It's taught me how to listen. I just listen so closely to the stories and songs, and think about the craft in a way that's really deep because I get to listen a lot, and witness.

I also just love how kind the songwriters are, generally. The ones that I've connected with are deep people. We all work multiple jobs, and so we have lots of sides to ourselves. I think it's a special place to be taught, through experience, how to live a life in music. I feel really grateful. And I keep coming back to Boston. I just like it here.