The 21st century on Broadway broke records straight from the jump. The biggest hit of the century came out of the gate immediately in early 2001: The Producers, which subsequently broke Broadway box office and Tony Award records (winning 12 awards). It was a feat that would not be matched until…2016, when Hamilton made Tony history by having the most nominations for a single show ever (winning 11 awards, so close).

These high points clearly show that contrary to the many hand-waving editorials about the death of the Broadway musical, the 2000s has been very good for musical theatre.

So when the editorial team at Playbill were thinking of ways to look back on the past 25 years in theatre, our thoughts went immediately to the thing that made all of us fall in love with this art form in the first place: music—the songs that grabbed us upon first listen, made us look up where it came from, and then led us to devour one musical…and then another.

But what constitutes the best songs of the last 25 years?

It’s not just a tune you can hum. Or a tune that comes from a Tony-winning score. In our opinion, it’s the song that has ascended beyond the show that it came from, the song that is a favorite pick at auditions, a mainstay on personal playlists, a streaming and radio chart-topper. It is also representative of a canonically great musical—the go-to example when someone asks you to name an opening number, an “I Want” song, an Act One closer, or an 11 o’clock number.

To create this list of the best showtunes of the 2000s, we at Playbill established some ground rules. These needed to be original songs written for a stage musical (no matter how much we love “Let Me Be Your Star” from Smash). They needed to have been performed on Broadway in the last 25 years (shows that premiered Off-Broadway and then moved to Broadway counted). And we could only pick one song per musical (we must spread the love after all). We spent hours debating which musicals must be included (as well as the hidden gems). We assembled multiple shortlists and had many hours of spirited debate.

At the end, we settled on a list of 30 songs, which we released in chronological installments beginning with 10 songs on December 22 and 10 songs on December 23. The full list of all 30 songs is now live.

Without further ado, here’s the Best Broadway Showtunes of the Last 25 Years (spanning the years 2000 to 2025)—with reflections from Playbill's editorial staff. 

Click on the link to jump to each year on the list.

2000 to 2004

2005 to 2009

2010 to 2014

2015 to 2019

2020 to 2025

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“Keep It Gay” from The Producers (2001)

If you weren’t following Broadway in the early aughts, you might not know just how big of a deal The Producers was. New York was freshly post 9/11 and looking to laugh, and The Producers was there to supply the experience. It’s one of those shows that just worked, from casting to staging to material—everything. Mel Brooks himself penned the musical’s book (with Thomas Meehan) and score (with the help of arranger Glen Kelly), telling the story of two shyster theatrical producers who endeavor to purposefully mount a Broadway failure, a musical called Springtime for Hitler. The scheme involves picking the most absurd creatives possible to mount the work, which they find in Roger De Bris, a… flamboyant… director-choreographer not so much known for historical dramas as for his showgirl-filled frothy musicals. The joke of “Keep It Gay” is that Roger is singing about finding a way to make a about bummer wars and mean old Nazis “happy” (referring to the mid-century definition of gay). But Roger, of course, is himself super gay (he has a “common law assistant”). Now, as a gay man myself, sometimes I pre-cringe returning to things that deal in over-the-top gay stereotypes. But I gotta say, “Keep it Gay” is just really funny. It never feels hateful, and it never feels unfair. Yes, it’s over-the-top, but it is a hyperbolized version of people I have met repeatedly in this industry, perhaps even including myself—FINE! It’s a real highlight of The Producers (and, in my opinion, the only scene worth watching in its rather uninspired 2005 movie version). —Logan Culwell-Block

“Good Morning Baltimore” from Hairspray (2002)

“Good Morning Baltimore” is not only one of the greatest songs of the 21st century, it is one of the greatest musical openers of all time. One could easily make a case for it being the best, or at the very least, in the top three (but being Baltimore-born, I may be biased). It accomplishes everything you could want from an opener: setting the scene, introducing the character, and a killer hook. Marc Shaiman and Scott Wittman also smartly made sure “Good Morning, Baltimore” doubled as an "I Want" song—by the end, we have a pretty good idea of who Tracy is, and where she's going in life with her bright eyes and big heart. The song is also a spot-on cultural representation of the spirit of a city. Talk to any Baltimore native, and you'll hear them declare Baltimore to be the greatest little city while cracking jokes about its quirks all in the same breath. It's called Charm City for a reason, and "Good Morning Baltimore" captures that charm perfectly, showing that a city is what you make of it, just like life. Even the song's notorious "oh-oh-ohs" in the verses feel referential, as it's very easy to throw in a good old Baltimore accent and make those "oh's" sound like "oeeeehhhhs," hon! —Meg Masseron

Not for the Life of Me from Thoroughly Modern Millie (2002)

Who didn’t study all the pictures in magazines and books of New York City before declaring that they would take the city by storm? Jeanine Tesori and Dick Scanlon’s music for Thoroughly Modern Millie is a pillar in the musical theatre canon, especially among those of us who grew up in the early 2000s; everyone wanted to play Millie Dillmount and sing absolute bops. “Not For The Life of Me” is, in my opinion, a perfect opening number with a delicious taste of an “I Want” song. In two minutes and eight seconds, the audience learns everything they need to know about their protagonist: She’s fearless and determined to create her dream New York City life, so confident that she will succeed that she rips up her ticket home. One minute in and you’re already rooting for her. I have the insane privilege of being a native New Yorker and when I saw Millie for the first time and heard this opening number, I was hooked, and inspired, and thought “She’s just like me! When I grow up, I’m gonna do that too. I’m gonna make it in Manhattan!” Except the ticket in my pocket was a MetroCard and I literally couldn’t tear it… My favorite part of “Not For The Life of Me” is how brilliantly it blends into the second song in the show, the title number that startlingly drops Millie and the audience into the “real world” hustle and bustle of Manhattan in 1922. The melody comes back around multiple times throughout the score and it’s just perfect. Boh-doh-dee-oh, baby! —Heather Gershnowitz

“I Can Do Better Than That” from The Last Five Years (Off-Broadway premiere 2002, Broadway premiere 2025)

This song is a defining example of ambition and musical storytelling, capturing a young woman’s electric mix of desire, defiance, and charm in the early stages of a relationship. From the opening measure, Jason Robert Brown sets a propulsive, almost conversational rhythm that mirrors Cathy’s restless energy and refusal to settle. His composition cleverly alternates between sprightly, almost syncopated verses and soaring, expansive choruses—reflecting Cathy’s swaying between practical observation and visionary dreaming. The bridge (my favorite part of the song) is the emotional and musical apex. It’s at this point the song truly pulls you in: You feel her longing not as abstract yearning but as a full-bodied, kinetic plan, a love letter to both ambition and hope. The combination of lyrical story telling, clever musical architecture, and that irresistible emotional surge is why I consistently come back to this song over and over again. And I’m clearly not the only one. The song (and let’s be honest, the entire score) has stood the test of time. Having premiered in Illinois in 2001, with two Off-Broadway runs, a featured film adaptation, and a belated Broadway debut just this year, The Last Five Years has squarely established its legacy in the musical theatre canon. Even as I type this, I guarantee someone is singing “I Can Do Better Than That” right now—in an audition at Ripley-Grier, at a senior showcase in Ohio, or maybe even just in a bedroom, recording a cover for TikTok. There is no clearer evidence that it is one of the great ballads from the last 25 years. —Jeffrey Vizcaíno

“Defying Gravity” from Wicked (2003)

In the past 25 years, no Act One closer has been as memorable, as meme-ed, as thrillifying as Stephen Schwartz’s “Defying Gravity” in Wicked. The image of Elphaba flying with a broom in her hand while vocalizing has become synonymous with Broadway. But “Defying Gravity” is not just the Act One Closer of Wicked. It is a vow between friends, a battle cry against enemies, an exclamation of ethos, and a proclamation of power. And, as much as the song marks the end of a first act of theatre (or first part of a two-part film), it also propels our protagonist out of her wide-eyed age of innocence. The song marks the beginning of Elphaba’s righteous pathway for equality for Animals and green girlies alike, the blessing bestowed to Glinda that she find happiness, and the first yellow brick thrown at physics itself! As a theatrical moment, it is unparalleled, literally cherry picked to provoke ooh’s, aah’s, and “yaaas girl”’s from every member of the audience. But the real perfection of the song is that it does not need the death-defying height and dazzling light to punctuate its power. “Defying Gravity” is just as spine-tinglingly satisfying when blasted out of car speakers or belted out in a karaoke booth. Whether you hear those opening notes at the Gershwin or at a drag show, and when you finally reach that climactic battle cry—you leave the song feeling like you, too, can ascend. That you can do anything. And that is what makes “Defying Gravity” one of the best showtunes of the 21st century. —Dylan Parent

“Fine Fine Line” from Avenue Q (2003)

It is now time to remind everyone that at the 2004 Tony Awards, where Avenue Q and Wicked were going head-to-head, the puppets beat the witches as Avenue Q took the coveted Best Score and Best Musical Tony Awards. Out of the many laugh-out-loud songs from Robert Lopez and Jeff Marx’s score, which also double as life observations (“The Internet Is For Porn” “You Can Be as Loud as the Hell You Want (When You're Makin' Love)”), it is the Act One closer, “Fine, Fine Line” that has endured well beyond the confines of its original production. In the context of the musical, the song serves as a heartfelt ballad sung by Kate Monster after her relationship with Princeton falls apart. While Avenue Q is largely defined by its irreverent humor and provocative storytelling, this number offers a striking contrast—a moment of sincerity and emotional vulnerability. Since the show’s debut, “Fine, Fine Line” has found a second life in auditions, cabarets, and concert performances, proving its emotional resonance long after leaving the puppeted street where it was born. —Meredith Ammons

“Lot's Wife” from Caroline, or Change (2004)

“Lot’s Wife”—from Tony Kushner and Jeanine Tesori’s Tony-nominated score for Caroline, or Change—is the 11 o’clock number for its title character, Caroline, a Black maid working for a Jewish family in 1963 Louisiana. It is the “Rose’s Turn” of the musical, exploring Caroline’s humble existence against the backdrop of social change prior to and following the assassination of President John F. Kennedy. While in “Rose’s Turn,” Rose is struggling to be seen, in “Lot’s Wife,” the dispirited and physically and emotionally exhausted Caroline is battling for her soul and salvation. Those fortunate enough to have seen Tonya Pinkins’ monumental performance in the original Broadway cast will likely never forget the palpable sense of despair that she conveyed throughout much of the show. Her performance of “Lot’s Wife” was a showstopper, opening her soul and battlefield-of-a-heart in the song, which builds to a full-voiced climax and then suddenly changes to almost a whisper. By invoking the Biblical story of Lot’s wife—punished for looking back—Caroline expresses her inability to change and how she’s “never been so good findin’ joy the way you should.” Through this defiant song, Caroline expresses her exhaustion, her resentment, and her overwhelming sense of being trapped on many levels, and ultimately asks God to “set me free. Don’t let my sorrow make evil of me.” Caroline knows letting go is difficult, but standing still is killing her. It’s a transformative 11 o’clock number. —Andrew Gans

“I'm Here” from The Color Purple (2005)

There are few things more thrilling in a theatregoing career than the moment you know, unshakeably, that a star has ignited before your very eyes: Cynthia Erivo singing “I’m Here” as Celie in the 2015 Broadway revival of The Color Purple was one of those moments. “I’m Here” has existed since the debut of the musical in 2005, when it was introduced to stunning effect by LaChanze. But sometimes, the simple beauty of a song can be overwhelmed by the trappings that adorn it, with an interlude and set reveal that interrupted the momentum of the song’s Broadway debut. Erivo’s rendition, featuring a new arrangement by Joseph Joubert and Catherine Jayes that cut the interlude, turned an excellent song into an extraordinary song, utilizing Erivo’s vocal instrument to the height of its abilities. Erivo’s rendition—which sees the put-upon and abused Celie finally learning to love herself—led to weeping in the aisles, shouts of praise mid-song, and the kind of emotional catharsis that has become all too rare on the commercial stage. It was the perfect alignment of song, singer, and story, and a theatrical experience unlikely to be equaled for many, many years. —Margaret Hall

“The Light in the Piazza” from The Light in the Piazza (2005)

Adam Guettel and Craig Lucas’ The Light in the Piazza is a fantastic showcase of a story that begs to be musicalized. Following an American mother and daughter on vacation in Italy, Guettel is able to use music to let his characters express themselves even when they cannot find the words. In the musical, Clara is 26 years old, but because of a head injury that happened when she was young, she is forever 12 emotionally. When she falls hard for an Italian boy, her mother writes it off to youthful fancies, something she needs to protect her daughter from. The beauty is: Clara really is in love and because of her condition, she just doesn’t have the ability—the words—to convey that. “The Light in the Piazza” is her impassioned attempt to do that to her mother. If you read Guettel’s lyrics, there’s not much going on. Clara remembers being in a Florentine piazza when she has a happenstance meeting with Fabrizio, and she fixates on the memory of what the sunlight looked like. Add in Guettel’s music, and you feel every bit of love, turmoil, excitement that is teeming just below the surface of her words—she knows the moment was big, but she can’t really process why. Clara doesn’t have the words to tell us how she feels, but feels she does. Guettel’s realization of that in this song is overwhelming—a masterpiece, and a stellar example of musical theatre at the height of its powers. —Logan Culwell-Block

"The I Love You Song” from The 25th Annual Putnam County Spelling Bee (2005)

Spelling Bee, as a musical, is mostly uproarious and silly. But the arrival of “The I Love You Song” suddenly wrenches the tone open to reveal something hauntingly human beneath the laughs. From the moment we hear the first plucked string of the sitar along with the haunting “ooo”s from Olive’s mother, the noise of the world recedes, and we are transported inside 11-year-old Olive’s mind. She sings into a space shaped by absence. Like most children, Olive is full of questions, but these questions have answers that are too mature for her to understand. When the voices of Olive’s absent parents join in, the harmonies intertwine in a way that feels like overlapping memories, familiar yet just out of reach. As the song continues, what began as a polite request has become a child’s desperate plea for connection. My favorite part of the song is Olive’s snap back to reality. As she spells the word “chimerical,” we are given the final dagger to the heart: “C-h-i-m-e-r-i-c-a-l. Highly unrealistic, wildly fanciful.” In that moment, we watch a childhood lost in an instant. Olive realizes that the thing she truly wants, more than winning the spelling bee…is the song we’ve all just experienced over the last five minutes. And tragically, it’s a dream. The title is deceptive. It is not a proclamation of love from parents to their child. It is the words that a neglected kid fantasizes about hearing. I treasure “The I Love You Song,” because it trusts stillness, because it is a masterclass example of William Finn’s skillful lyrical storytelling. And because every time those harmonies rise together, they remind us how powerful it is to name the love we needed, even if it arrives only in song. —Jeffrey Vizcaíno

“Show Off” from The Drowsy Chaperone (2006)

“Show Off” from The Drowsy Chaperone is the campy, tongue-in-cheek, overindulgent moment we want from any leading lady. Lisa Lambert and Greg Morrison’s tune starts as a demure and modest ballad to the stylings of what sounds like a Golden Age classic, then drops into an easy swing, disguising the twists and turns the rest of the number has in store. We then get a whole circus instrumental break, full of slide whistles, horns, a swooning waltz, and even a snake charmer section. Once you hear that timpani roll, it pays off with an ever-so-satisfying modulation accompanied with the genius lyrics, “I don’t wanna change keys no more.” And just when you reach that brassy belt indicating the end of the song you get hit with, “I don’t wanna encore no more.” This song is the gift that keeps on giving and not to mention the perfect playground for a diva to show us all of her chops. —Vi Dang

“Totally Fucked” from Spring Awakening (2006)

“There’s a moment you know you’[ve written an iconic song].” The early 2000s took the young person’s angst + rock score formula from Jonathan Larson’s Rent and ran with it. In using a punk rock sound to tell the story of German teens living in a repressive 1891 village, Duncan Sheik and Steven Sater made the 19th century immediate to young people living today. In particular, “Totally Fucked” changed the game in its portrayal of teen rage, dramatizing the moment when the young Melchior realizes all of the adults in his life were lying to them. What better lyrics to express those too-intense-to-put-into-words emotions than “blah blah blah blah blah blah blah”? It’s a second-act showstopper you’ll never forget, the Tony Awards performance that launched thousands of theatre kids—and a perfect anthem for group-singing on a road trip, a song that is a banger even outside the context of the musical it was written for. “Totally Fucked”… more like, “Totally! F*ck [yeah]!!”  —Ethan Treiman

“Omigod You Guys” from Legally Blonde (2007)

Omigod, you guys...Legally Blonde's opener is one to remember. From the very first riffs of guitar as the Delta Nus take to the stage, this song is electrifying to listen to, with bright vocals and catchy instrumentals. It's packed full with clever and funny lyrics, and the energy of it perfectly encapsulates the essence of Legally Blonde. From film to stage, it can be hard to tonally recreate what audiences already know, especially without using the pop song that opens the film. But "Omigod You Guys" provides the same bubbly feeling. From a storytelling standpoint, it also brilliantly sets up the rest of the show. Though "Omigod You Guys" introduces us to Elle Woods, it also keeps its focus on the heart of Legally Blonde: Elle's sorority sisters, who serve as more than just her personal Greek chorus throughout the story. They are also her friends, who give her the love she's been searching for, and teach her to find that same love for herself so she can succeed. Female friendship, definitely something worth singing about. —Meg Masseron

“96,000” from In the Heights (2008)

If In the Heights taught us anything, it’s that a showtune can be both a joyous block party and a profound mirror for our collective hopes. “96,000” stands at the very center of that truth. What gets me every time isn’t just Lin-Manuel Miranda’s lock-step rhythms and the way every character’s voice seems to spark off the next—it’s also how that layering (voices interweaving dreams, fears, and laughter) makes the whole ensemble feel like a single heartbeat yearning for something more. As the song unfurls, each imagined wish (escaping financial strain, investing in education, dreaming of a loft downtown) doesn’t feel like empty fantasy of onstage characters; it feels like our dreams because Miranda’s writing invites us into those lives so intimately. When the chorus swells, we’re singing alongside them in spirit. That’s partly why “96,000” has resonated so widely. It isn’t just a catchy hip-hop-infused showpiece, it’s a celebration of voices and cultures often sidelined on Broadway. And it helped propel the show into popular consciousness as something vibrant, authentic, and necessary. Audiences respond to it because the premise, “What would you do if you suddenly had a chance?” is universally human. Yet the execution is rooted in the specific, joyful, sometimes messy texture of Washington Heights life. That is why theatre lovers return to the Heights again and again with a grin, a lump in the throat, or both at once. —Jeffrey Vizcaíno

“I Miss the Mountains” from Next to Normal (2009)

If one is unable to truly experience the highs and the lows, is life really worth living? That’s the question addressed in “I Miss the Mountains,” one of the many great songs from the Pulitzer Prize-winning Brian Yorkey-Tom Kitt musical Next to Normal. Diana Goodman, a wife and mother whose struggle with bipolar disorder forms the core of the musical, sings the powerful ballad, sitting alone on the bathroom floor; the song ends with Diana’s somewhat tortured decision to flush her medication. Alice Ripley, who created the role of Diana Off-Broadway and subsequently on, won a Tony for her riveting performance. Ripley’s rock belt was the perfect vehicle for the song, in which the mountains are a metaphor for life’s ups and downs that once made Diana feel fully alive. The haunting melody is matched by equally haunting lyrics: “Mountains make you crazy / Here it's safe and sound / My mind is somewhere hazy / My feet are on the ground / Everything is balanced here / And on an even keel / Everything is perfect / Nothing's real.” As the song concludes, a resolute Diana realizes, “I miss the mountains / I miss my life.” And we miss the song too, after it ends, which is why we immediately want to listen to it again. —Andrew Gans

“Get Out and Stay Out” from 9 to 5 (2009)

If you need a song to belt out in the car, shower, at the gym, or at Marie’s Crisis, “Get Out and Stay Out” is that girl. Screlting this one after a break-up? An experience only comparable to breaking dishes in a rage room. Being that 9 to 5: The Musical was created by the ultimate HBIC, Dolly Parton, it only makes sense that there would be a power ballad of this magnitude rooted in claiming one’s ownership as an independent woman. This 11 o’clock number was the first time in my theatre-going life that I experienced the audience around me hold their breath with their hands ready to clap like their lives depended on it—they could not wait for Stephanie J. Block to get to the end of the song and applaud. “Get Out and Stay Out” is a showtune you can listen to over and over again at various points in your life and relate to it differently each time. It’s a song I often gravitate toward whenever I need to light a fire under my ass or need the confidence to stand up for myself. It’s also the best showtune to put at the end of your running playlist, the last 55 seconds can get you across any finish line (try it, seriously). —Heather Gershonowitz

“Hello!” from The Book of Mormon (2011)

“Hello”—from Matt Stone, Trey Parker, and Robert Lopez’s wonderfully sacrilegious The Book of Mormon—is one of the defining opening numbers of the century. And if you don’t think so, “goodbye.” It’s clever, charming, and (all things considered) pretty simple, as far as Broadway openers go. It’s the same melodic refrain over and over again, with different lyrics, layered over each other, as it introduces you to the different Mormon missionaries in the musical (and the one missionary, Elder Cunningham, who doesn’t follow the tune is the one you have to watch out for). This neat cacophony of overlapping melodies culminates in sparkling harmonies that launch you, smiling, into the show. (Plus, the song contains one of my all-time favorite lyrical jokes: “So you won’t burn in hell-ooooo!”) Has it ever been so much fun to be proselytized to? —Ethan Treiman

“Revolting Children” from Matilda The Musical (2013)

“Revolting Children” is the rabble rousing 11 o’clock number penned by Tim Minchin from Matilda the Musical. The song begins with one of the students wailing out a battle cry, rallying up the ranks of children to revolt against the enemy: Mrs. Trunchbull. Once the chorus hits, the song plows through to the end, taking you through a sonic journey of disco, British rock, funkadelic guitar, blaring horns, and tight harmonies. It’s a rebellious anthem of liberation and reclaiming your power. “Revolting” takes on a double meaning in this protest, meaning both disgusting and the act of rising in rebellion. For anyone who loves an easter egg, the lyrics also cleverly give a nod to Roald Dahl’s Revolting Rhymes. Whether you’re a defiant kid or you have a mutinous spirit, this song is your call to revolution. —Vi Dang

“Not My Father's Son” from Kinky Boots (2013)

When Broadway musicals get announced with pop songwriters supplying the score, sometimes we theatre snobs may turn our noses a little prematurely. For some reason, we get worried that it takes a “real” theatre person (whatever that means) to write a “real” musical. But then there’s people like Cyndi Lauper, who over her pop career has more than proven that she’s both skilled at crafting an ear-worm melody (“Girls Just Wanna Have Fun”) and incredibly thoughtful, emotion-driven lyrics, too (“True Colors”). Kinky Boots book writer Harvey Fierstein once said that he knew Lauper was the right songwriter for the show when she submitted one of the first things she wrote for it, “Not My Father’s Son.” If you listen to it, it’s not hard to see why Fierstein had that reaction. The song has a beautiful melody, but its lyrics show how much Lauper understood the story and characters of Kinky Boots. The song comes in the moment of the story when straight-laced (pun intended) shoemaker Charlie Price and drag queen Lola (aka Simon from Clacton) figure out they’re not so different from each other as they might have thought: both have daddy issues! It’s gorgeous, introspective, and raw—and immediately accessible to anyone who has dared to not live up to their parents’ expectations. —Logan Culwell-Block

“One Second and a Million Miles” from The Bridges of Madison County (2014)

Despite it running on Broadway for only four months, Jason Robert Brown’s score for The Bridges of Madison County has had immense staying power—it’s become a favorite in senior showcases, auditions, and cabaret sets. The score is sweeping, earnest, unabashedly romantic, and lends itself to some thrilling vocals. The most potent example is the second act duet, “One Second and a Million Miles,” where roaming photographer Robert is trying to convince Francesca to leave her family and run away with him. That means the song itself needs to be irresistible; Brown accomplishes that in spades, with Steven Pasquale’s “come with me” ringing high and clear as a bell in the first verse before Pasquale and Kelli O’Hara’s voices meld together in a chorus that can only be described as a musical orgasm. It’s a spirited debate, an admission of love, and a feat of storytelling all in one—the characters end the song in a different place than when they started, and we as listeners feel like we’ve been taken on a journey that we want to repeat again and again. —Diep Tran

“Alexander Hamilton” from Hamilton (2015)

It would be impossible to discuss Broadway’s best songs of the 2010s without mentioning Hamilton. And while it was incredibly challenging to choose just one song from Lin-Manuel Miranda’s era-defining score, we had to give it to the opener. The show’s opening number, “Alexander Hamilton,” sent shockwaves through pop culture from the first time it was performed: In 2009 when Miranda sang it solo at an event hosted by President Barack Obama. Then just an idea called The Hamilton Mixtape, you can tell the song was special; it has changed very little since that 2009 performance. From the very first seven notes, audiences were instantly hooked. Beyond the undeniable catchy melodic refrain of “Alexander Hamilton…,” Miranda’s lyrics expertly prepare listeners for the two hours and forty-five minutes journey ahead. The song introduces the audience to the show’s protagonist through a cleverly rapped account of his life before arriving in America, told by his lifetime rival Aaron Burr. In doing so, it not only establishes who Alexander Hamilton is, but also lays the foundation for his ambitions and motivations, and his eventual death—all set to a beat that puts you at attention immediately. —Meredith Ammons

“Ring of Keys” from Fun Home (2015)

Jeanine Tesori and Lisa Kron’s “Ring of Keys” is a rare song that really trusts its audience. We don’t need the lyrics to say: “I’m gay, I’m so excited to discover I’m gay!” Instead, this ballad from Fun Home trusts a list of ordinary objects (“your swagger and your daring and the just-right-clothes you’re wearing / Your short hair and your dungarees / And your lace up boots / And your keys, your ring of keys”) to communicate a moment of profound personal discovery. I think that’s more aligned with our lived, human experience—where the world around us stirs emotions within us before we even have time to process them (or years to write a graphic novel about them). Not to mention, Sydney Lucas’ fierce rendition of “Ring of Keys” at the 2015 Tony Awards shows that you don't need spectacle to deliver a remarkable performance. A great song in the hands of a talented singer is more than enough. —Ethan Treiman

“Waving Through a Window” from Dear Evan Hansen (2016)

"Waving Through a Window" from Dear Evan Hansen is arguably the song that made this show a masterpiece. The song accomplishes with the audience the very thing the socially isolated Evan himself seeks from his peers: understanding, empathy, and grace. Without it, the inclination to forgive Evan for his eventual missteps and wrongdoings just isn't there. In addition to its beautifully grassy, organic sound (with violin and acoustics that fill listener's ears with an earthy rawness that doesn't require big booming instruments to feel full), "Waving Through a Window" is a masterwork of lyricism. The song's introduction is contradictory: Most of the song is Evan asking if he'll ever be noticed, but the opening lines express that he has learned to withdraw to avoid rejection: "no slipping up if you slip away / So I got nothing to share / No, I got nothing to say." This song is more than an outsider’s anthem, it’s a plea to be seen and heard punctuated by a soaring chorus that envelopes Evan's soliloquy of loneliness in climactic waves—a poetic device of musical irony. Even with Dear Evan Hansen no longer running on Broadway, this song lives on as a comforting shoulder to cry on for anyone who feels invisible—whether you're neurodivergent, experiencing bullying or marginalization, or just aching to be seen. —Meg Masseron

“She Used to Be Mine” from Waitress (2016)

Even thinking about “She Used to Be Mine” from Waitress is enough to bring me to tears. The song, penned by Sara Bareilles, comes at Jenna’s emotional breaking point: She is pregnant with her abusive husband’s child, and he has just stolen the money she had secretly saved to escape him. At her absolute lowest, Jenna reflects on the woman she once was—before marrying Earl, before the loss of her mother—when she still carried a sense of hope and self-worth. That spark briefly reemerges through her affair with Dr. Pomatter, which also highlights how far she feels she has fallen. The song is a devastatingly beautiful moment of introspection, capturing a woman mourning the future she imagined for herself and aching to believe that a better life is still possible. She is messy, but she’s kind, and she sings a killer song. —Meredith Ammons

“Dust and Ashes” from Natasha, Pierre & The Great Comet of 1812 (2016)

For my money, this existential ballad is the best showtune of the 21st century so far. Written by Dave Malloy specifically for the musical’s Broadway leading man, Josh Groban, what begins as a deeply insular search for meaning and purpose blossoms into a full company aria, proclaiming the value of life, love, and being attuned to the present moment. Interweaving a variety of Tolstoy quotes, with lyrical references to Bob Dylan, the final product is a soul-shaking depiction of depression, and the desperation to surface after years of struggling to survive. Audiences didn’t know how lucky they were when this song was being performed on Broadway eight times a week. —Margaret Hall

“Omar Sharif” from The Band's Visit (2017)

Written by master-melodist David Yazbeck, “Omar Sharif” is a sonic wave, enveloping you in multi-sensory warmth. Like the show itself, the song is a perfectly faceted prism of cultural exchange, with elements of classical Arabic music interwoven with the sweeping melodies of traditional musical theatre—both combine into a truly exemplary story song about a young woman’s love for cinema, which transported her away from the mundane town where she lived. In less than 3 minutes and 30 seconds, Yazbeck transforms leading lady Dina from intimidating to enchanting, sweeping listeners away on the jasmine wind alongside her. The genius melody uplifts the evocative lyrics that is likely to leave even the most cynical listener overwhelmed with the taste of a life they themselves have not lived. It is, from every angle, enigmatic perfection. —Margaret Hall

“Wait For Me” from Hadestown (2019)

Anaïs Mitchell’s “Wait For Me” is the kind of song that makes stones, and anyone listening to it, weep. Narratively, it is so self-contained that it makes exposition feel elegant. You listen to this song and you know the characters, the stakes, and the rules of their universe. At the same time, the song serves an important function in the story: It is a song that needs to be powerful enough to split open stone walls, allowing Orpheus entry into the Underworld to go after his love Eurydice. And Mitchell’s haunting melody more than succeeds, bringing me goosebumps every time I hear that swell of “wa-aa-aaiii-t for me, I’m comin.’” It sticks in your mind immediately after hearing it. “Wait For Me” also edges out Hadestown’s other songs due to the ferocity of the “Wait for Me” (reprise). Taken together, well it’s musical theatre perfection. By the end of it, I got my red neckerchief tied tight, my boots strapped to my feet, my heart open, and my spirit set for adventure. Where do I think I’m going? I think I’m going to get the love of my life! For a song to do that? That’s wild. —Dylan Parent

“Inner White Girl” from A Strange Loop (2022)

What makes an “I Want” song such an important part of any musical theatre score is it establishes character motivation and makes the audience empathize with the person singing it. Many times, the thing that the character wants is something we can all relate to. But what’s particularly brilliant about “Inner White Girl,” the “I Want” song from Michael R. Jackson’s Tony and Pulitzer-winning musical A Strange Loop, is how unapologetically specific it is—the song and musical isn’t trying to appeal to everyone, and it’s better for it. The musical is about a young Black gay man named Usher who is trying to write a musical and make his way through a world that is antagonistic to Black gay men. “Inner White Girl” has the sensitive, artistic Usher singing about his desire to have the social freedoms usually afforded to white women: “cool, tall, vulnerable and luscious” and “wild and unwise.” Usher’s sheer honesty and yearning is something immediately accessible to anyone who has ever felt marginalized, who is ashamed to show the world who they truly are. There’s a reason why I have a necklace that says “Inner White Girl,” because through its hyperspecificity, Jackson’s song touches on something achingly real. —Diep Tran

“Anagram” from Kimberly Akimbo (2022)

“Anagram,” from Jeanine Tesori and David Lindsay-Abaire’s Tony-winning score for Kimberly Akimbo, captures such a sweet moment between Kimberly, a teenager with a rare aging disorder, and her schoolmate Seth. As the latter is voicing the creation of an anagram for “Kimberly Levaco”—one that gives the musical its title—Kimberly is sharing her ever-growing feelings for Seth, and the effect is utterly moving. There is something magical about Victoria Clark’s gentle “ohs” amid Seth’s anagram solving that pulls at the heartstrings and doesn’t let go. The song builds beautifully until the anagram is complete and the listener is rooting for this unlikely romance between the two students. It’s no wonder the performance earned Clark her second Tony Award. She is utterly hypnotizing, falling for her young friend (Tony nominee Justin Cooley), and the open heartedness of both actors makes the song a triumph over adversity. —Andrew Gans

"When You're in Love" from Maybe Happy Ending (2024)

Modern musical theatre tends to lean towards vocal acrobatics, with composers seemingly in a competition to see how high they can get their stars to belt (also known as the Wicked effect). Hue Park and Will Aronson’s Maybe Happy Ending is a refreshing change of pace (and volume). The beauty of the show’s Tony-winning score isn’t through delivering high notes; it’s in its restraint. “When You’re in Love,” which was the first song ever released by the Broadway production, showcases this beautifully. The show is about two retired HelperBots who discover a new purpose in life through connecting with each other. While a typical musical theatre score would contain an upbeat song about the ecstasy of falling in love, “When You’re in Love” revels in its melancholy. Note the simple piano under the disarmingly complex first verse: “When you’re in love, you are the loneliest. You’re only half, when one is what you were.” That’s the show’s thesis in a nutshell: Love is wonderful, but it is also fragile. Is love worth the inconvenience, the pain? As the song and orchestration build—and the doubt-filled lyrics give way to hope and gorgeous harmonies from performers Darren Criss and Helen J Shen—“When You’re in Love” answers that question. There is nothing like falling in love, and there is nothing like Maybe Happy Ending. —Diep Tran