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 will be released in chronological installments beginning December 22 and December 23. The full list will be released December 24.

Without further ado, here’s the Best Broadway Showtunes of the Last 25 Years, Part One (spanning the years 2000 to 2005)—with reflections from Playbill's editorial staff. Check back tomorrow for Part Two: 2006 to 2014, and Wednesday for Part Three: 2015 to 2025.

“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 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