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Everyone knows the tune. You’ve probably hummed it while getting ready for a date or jokingly sang it in the mirror after a particularly good haircut. I Feel Pretty from West Side Story is one of those cultural touchstones that feels like pure, unadulterated sunshine. It’s bubbly. It’s pink. It’s Leonard Bernstein and Stephen Sondheim at their most accessible. But if you actually sit down and look at where this song sits in the timeline of the show, it starts to feel a lot less like a self-love anthem and a lot more like a tragedy waiting to happen.
Most people see Maria twirling around the bridal shop and think "Oh, how sweet, she's in love."
They're wrong. Well, they aren't entirely wrong, but they're missing the point. The song is actually a masterclass in dramatic irony.
The Gap Between Maria’s Joy and the Audience’s Dread
When Maria sings I Feel Pretty West Side Story fans usually experience a specific kind of pit in their stomach. Why? Because while Maria is singing about feeling witty, bright, and charming, the audience knows something she doesn't. In the 1957 stage play and the 1961 film, this number happens right after the rumble.
Think about that for a second.
Maria is celebrating her beauty and her love for Tony, completely unaware that Tony has just killed her brother, Bernardo. It’s brutal. The contrast between the upbeat, triple-meter rhythm—it’s essentially a waltz—and the literal blood on the streets just a few blocks away is what makes it work. It’s not just a "pretty song." It’s a shield. It is Maria’s last moment of true, naive innocence before her entire world gets incinerated.
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Sondheim himself actually famously hated his own lyrics for this song. He thought they were too "purple." He once mentioned in an interview that a girl like Maria, who had just moved from Puerto Rico and didn't have a massive English vocabulary, wouldn't use words like "enticing" or "alarming." He felt he was showing off his own cleverness rather than writing for the character. But despite his self-criticism, the song stayed. It’s too catchy to kill.
How the 2021 Spielberg Version Changed Everything
Steven Spielberg and screenwriter Tony Kushner did something very specific with I Feel Pretty in the 2021 remake. They moved it. In the original versions, the song happens after the rumble. In the 2021 film, they shifted the timeline so the song happens before the rumble.
This changes the entire vibe.
Instead of the song being a tragic display of ignorance, it becomes a final burst of hope. In the 2021 version, Maria is working a night shift at Gimbels department store. The setting is more grounded. You see the grit of 1950s New York. When Rachel Zegler’s Maria starts singing, it’s about a girl who feels like she finally has a future in a city that usually looks down on her. It’s less about the "dramatic irony" of her brother’s death and more about the fleeting nature of the American Dream.
Is it better? Hard to say.
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The original placement makes you want to scream at the screen to warn her. The 2021 placement makes you mourn for the happiness she’s about to lose. Both work, but for totally different emotional reasons.
The Technical Brilliance of the Music
Bernstein was a genius because he knew how to make complicated music sound simple. I Feel Pretty is written in $3/4$ time, which naturally gives it that swaying, dance-like feel. But he throws in these little "stings" and syncopations that keep it from being a boring ballroom dance.
The song relies heavily on the "I feel..." motif.
It’s repetitive.
It’s catchy.
It’s designed to get stuck in your head.
But look at the lyrics. "I feel pretty and witty and bright / And I pity any girl who isn't me tonight." That's not just a girl in love; that's a girl who is high on the feeling of being seen. Maria has spent her life being Bernardo’s little sister or a seamstress in a shop. Tony makes her feel like a protagonist. The music reflects that ego boost. It swells and soars. It feels expensive.
Why Sondheim’s "Cringe" Is Actually Good
As mentioned, Stephen Sondheim was his own harshest critic. He felt the internal rhymes—like "it's alarming how charming I feel"—were too sophisticated for a teenage girl from the East Side. He called them "theatrical."
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But honestly? That’s why we love it.
Musical theater is heightened reality. We don't go to see West Side Story for a documentary-style look at street gangs. We go for the emotional truth. The "pretty-witty-bright" line works because it captures that specific, giddy feeling where you feel like you’re starring in your own movie. When you’re in love for the first time, you do feel witty. You feel like the smartest, most beautiful person in the room. Sondheim accidentally captured the arrogance of youth perfectly, even if he thought he was just being a "wordy" writer.
The Enduring Legacy of the "Pretty" Girl
This song has been covered by everyone from Julie Andrews to Little Richard. It’s been used in commercials for everything from makeup to cars. It has survived because it taps into a universal desire to be transformed.
In the context of the show, the song serves as the "calm before the storm." Without it, the second act of the musical would be almost too dark to bear. You need that moment of light so that the eventual ending—the death of Tony, the breakdown of the gangs—actually hurts. You have to see what they’re losing. Maria’s joy is the stakes. If she doesn’t feel "pretty," the loss of that feeling doesn't matter.
What You Should Take Away From It
If you’re watching the movie or the play for the first time, pay attention to the lighting and the colors during this number. In almost every production, the colors are at their most vibrant here. It’s the peak of the "Technicolor" dream.
To really appreciate the song, try these steps:
- Listen to the 1957 Broadway Cast Recording: Notice how Marni Nixon (who dubbed Natalie Wood in the 1961 movie) brings a more operatic, formal tone compared to Rachel Zegler’s more contemporary, breathy interpretation.
- Watch the transition: If you’re watching the 1961 film, pay attention to the very next scene after the song ends. The jump-cut from Maria’s smiling face to the grim reality of the streets is one of the most famous edits in cinema history.
- Analyze the backup singers: The "Shark girls" (Rosalia, Consuelo, etc.) act as a reality check. They tease her. They remind us that Maria’s obsession with Tony is bordering on the "crazy." It grounds the song so it’s not just a floating solo.
Ultimately, the song isn't about vanity. It’s about the brief window of time where a person can feel invincible before life gets in the way. Whether you prefer the tragic irony of the original or the hopeful longing of the 2021 version, the song remains the beating heart of Maria’s character. It’s the moment she chooses her own identity over the one her family gave her. And that’s a lot more "witty and bright" than people give it credit for.