"West Side Story" is one of musical theater’s greatest triumphs. Its score by Leonard Bernstein is one of the most famous pieces of music in modern history, and it even won Best Score Soundtrack for Visual Media at the GRAMMY Awards in 1962. Now, Steven Spielberg’s film adaptation of the 1957 masterpiece is up for seven Academy Awards, including Best Picture and Best Sound.

Yet, for six decades, the song "I Feel Pretty" — sung by Maria and the other Puerto Rican women in a department store dress shop — haunted lyricist Stephen Sondheim, who wrote the iconic song at age 25. "I’ve shot my mouth off for years about how I am not happy with 'I Feel Pretty,'" he once told "60 Minutes."

In the original 1957 Broadway production, the song follows the big rumble where Maria’s lover, Tony, kills her brother, Bernardo. Only Maria has no idea this happened. In the Robert Wise directed 1961 film, "I Feel Pretty" precedes the rumble — a placement Sondheim preferred.

Additionally, Sondheim was never a fan of the lyrics he wrote for "I Feel Pretty" and considered the diction to be out of character for Maria. "Can you imagine a Puerto Rican girl who just arrived in the country…singing 'it's alarming/how charming/I feel?'" he said to "60 Minutes." In the most recent 2020 Broadway revival of "West Side Story," the song was cut from the show.

Spielberg and screenwriter Tony Kushner solve the diction issue by recontextualizing the "I Feel Pretty" scene. In the 2021 film, Maria (Rachel Zegler) and her friends work at the department store as after-hours cleaners. As Maria sings "I Feel Pretty," the camera shows numerous marketing signs in the store; the audience assumes that Maria is taking the words she reads in the store marketing and using it in song.

In a recent Directors Guild of America panel, Spielberg addressed the consideration of cutting the song: "The only one on my side was Stephen Sondheim. We both wanted to cut 'I Feel Pretty.'" According to Den of Geek, Spielberg noted it had "less to do with Sondheim’s retroactive disdain for the self-aware lyrics he wrote and more to do with Spielberg’s intent on staying as close to the structure of the original 1957 Broadway production of 'West Side Story' as possible."

To bring that vision to life, the creative team hired Composer Jeanine Tesori (Shrek; Thoroughly Modern Millie) as the film’s development music consultant and supervising vocal producer. She’s been collaborating with Kushner for 25 years including on the most recent 2021 Broadway revival of "Caroline, or Change." She spoke with GRAMMY.com all about the behind the scenes  of bringing "I Feel Pretty" to the silver screen.

Tell me about your process of recording and filming "I Feel Pretty" from a music perspective.   

A thing that sometimes gets ignored in a musical is the placement of a song and the energy that it receives from what just happened. The audience knows that there's been a tragedy. This is the last time that these women, especially Maria, will ever experience true joy. As soon as she knows [about the rumble], her life is over and the audience knows that. That's the power of "I Feel Pretty" …this incredibly joyous song when the audience knows this information that no one else [on screen] knows.

"I Feel Pretty'' is a song that had a dual purpose. Steve [Sondheim] was always bothered by the language [he wrote for Maria to sing] — where does she get "alarming?" Instead of fighting it, what Tony [Kushner] did was set the scene in Gimbels using words [on signs in the store] like "witty and bright." [Maria’s] taking in the language as she cleans.

Any time that you direct a lyric [as a vocal coach], it has to be in alignment with what a director wants. I had said to [Spielberg] that I've never really seen "I Feel Pretty" where the first line is a discovery. When we originally were talking about "I Feel Pretty," I said, "What if 'I Feel Pretty' is not a given? What if this is something read for the first time?" This is the first time [Maria’s] actually felt that way, and surrounded by brightness and lightness with the fact that she's loved, and that you see all these Brown women cleaning. Our job was to make it as joyous as possible, but also grounded in something.

What were the discussions about the song before filming even began?   

If we cut it, what would be missing? You can't cut it because of the power of a young girl when she has her last moments of happiness. And we know the oncoming storm. The fact is: Maria doesn't get to sing that much in West Side Story. She sings "I Feel Pretty," "Tonight" and "One Hand One Heart," but she doesn't have a solo. So when you really look at it, you have to have that song for her.

Did Steven Spielberg ever consider giving it the chopping block?  

I never really took it seriously that we were ever going to cut it. It's West Side Story. Our job was always to find a way to make it feel like you had to have it. It was inevitable.

How long did you work on the vocals for this particular scene?  

We did a bootcamp. Then we were in rehearsals for a long time, six weeks, before we started shooting. Once you start pre-recording, you start really shooting the movie.

I wanted the singers to understand the writing; I wanted them to understand what I thought the composer and the lyricist were doing. We had Steve so we could ask him what he was doing when he was alive. The trick was to be late enough [in recording the vocals] that I knew what the acting choices were that were being made so they could stay true to what they were doing. If we had done it earlier, we would have had to have done all of it again.

When you have a masterwork like this…you sing it into being. The job is to make people really believe that this is happening in the moment, and that you're actually inventing it. That is not so easy to do. There was a point in time where no one had ever heard [this score] before. So it's really thinking about it as a new work.

What specific direction did you give Rachel and the cast?  

When you're singing a song like "I Feel Pretty," you actually don't have to sound pretty. The music takes care of that. There's a little bit of intention: It's not to sound ugly, but it's to sound true. You don't need to sound pretty, to feel pretty.

What changes did Stephen Sondheim offer, if any?  

For "I Feel Pretty," I don't think any.

What did he think of the final version?   

I know that he loved the film. He was so excited by it. The thing I always loved about Steve, having known him most of my life, was that even though he aged, his delight was always palpable. When he heard something that delighted him or surprised him, he was so happy about it. And that's what I felt about this version. You just didn’t know what was going to happen next. I think it's so beautiful that this was the last thing that, as I understand it, he got to see.

And he was happy with how "I Feel Pretty" came out in the end?   

That's what he told me. I have to believe him. I think he was very happy about it. I think it settled something that had been pulling at him since he wrote it. It incorporated what had been pulling at him as opposed to rewriting it.

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