The ‘ITS’ Lists: The Top Five Musicals of the Last 25 Years

Posted in Blog, What's Streaming? by - October 14, 2025
The ‘ITS’ Lists: The Top Five Musicals of the Last 25 Years

Musicals. You either love them or you hate them. And if you love them you tend to really REALLY love them. That love tends to be really really personal for us fans. For a movie musical to work for you, the film itself not only has to be good, but the music has to resonate. That is going to be different for everyone.  

So, in saying that I know, that there have been some really great musicals to grace our screens since the 2000s began.  Some of them aren’t on this list, but there’s only five! So for fans of The Greatest Showman, I know you’re out there.  Be proud, I hear you, I still sing along with Hugh and company regularly, but you just missed out.  Rocketman? Also a great movie.  West Side Story? Beautifully shot.  Cats? Well, don’t make me laugh. 

To celebrate the release of a new movie musical to the fold, Kiss of the Spider Woman, starring Jennifer Lopez, Diego Luna, and Tonatiuh, below are my top 5 musicals of the last 25 years.

In the Heights

Okay, so I feel it’s weird putting just part one of a movie on the list when part two isn’t out, so while the first half of Wicked was wonderful, spoiler alert, you won’t find it here.  What you will find is this exuberant and joyful film also directed by John M. Chu.  In The Heights comes with music from Lin-Manuel Miranda that celebrates his Latin heritage while acting as a preview for the style that would eventually become the juggernaut that is Hamilton.  

This very cinematic musical tells the story of Usnavi (Anthony Ramos) who dreams of returning to the Dominican Republic to buy back his father’s bar.  But he also dreams of of Vanessa (Melissa Barrera) who yearns to get out of Washington Heights and find an apartment downtown.  Every character portrayed by the talented cast has their own hopes and dreams. This feel-good celebration of community, life and love was a welcome back to cinemas after COVID, and as close to an old Hollywood musical as we had seen for a while at its release in 2021.

Women are dancing in front of brownstone

Cr. COURTESY OF Likely Story

Tick, Tick… Boom!

As someone whose favourite musical is Rent, I would have loved to be able to include that show’s 2005 film iteration in this list.  Sadly, despite having most of the Broadway cast in its ranks, it just wasn’t that good.  But I’m happy to have this musical, also penned by the late Jonathan Larson, be more than worthy of a top spot.  It’s a semi-autobiographical show that chronicles Larson preparing a workshop for a musical called Superbia.  

Directed by Lin-Manuel Miranda (yes, I guess he kind of gets two entries on this list but he just seemed to be everywhere around 2021), Tick, Tick…Boom! earned star Andrew Garfield a Golden Globe for his portrayal of Larson as well as an Academy Award nomination.  Broadway fans will find the scene at the Moonlight Diner particularly full of joy since so many veterans of the stage find their way to the seats, and Rent fans will be able to hear the beginnings of their favourite songs amongst this show’s numbers.  The only thing bad about Tick, Tick… Boom! was that Netflix only gave it a short limited release in theatres before it landed on the streaming service. 

VANESSA HUDGENS as KARESSA, ANDREW GARFIELD as JONATHAN LARSON

tick, tick…BOOM! (L-R) VANESSA HUDGENS as KARESSA, ANDREW GARFIELD as JONATHAN LARSON in tick, tick…BOOM!. Cr. COURTESY OF NETFLIX

Moulin Rouge!

Putting a jukebox musical on the list feels almost like cheating.  In fact Moulin Rouge! has only one original song, ‘Come What May’.  And that song was even originally written for another of director Baz Luhrmann’s films, Romeo + Juliet. This disqualified the song for Oscar contention. But no worry, the film won two other Academy Awards and was nominated for Best Picture as well as earning a nod for star Nicole Kidman.  

Moulin Rouge! tells the love story of Satine (Kidman), a courtesan who works at the famed nightclub and Christian (Ewan McGregor) a poor Bohemian poet.  Luhrmann spent years securing the rights to all the popular songs in the film, including Nirvana’s ‘Smells Like Teen Spirit’, Elton John’s ‘Your Song’ and Sting’s ‘Roxanne’.  Presented largely in medleys sung by the film’s stars, the juxtaposition of modern music with 1890’s Paris was unique.  This 2001 movie, shot with frenetic energy by Luhrmann was like nothing I’d ever seen before.  Or since.  

A woman and a man in front of a curtain

Cr. COURTESY OF 20th Century Fox

La La Land

Still one of my favourite films in recent memory, director Damien Chazelle really captures the Hollywood musical feel from its very opening scene on the Los Angeles freeway.  In a colourful, choreographed number, the scene appears as a one-shot (even though it’s three) as drivers exit their cars during a traffic jam to sing “Another Day of Sun.”

La La Land features music by Justin Hurwitz with lyrics by Benj Pasek and Justin Paul (who are also known for their work on The Greatest Showman and Dear Evan Hansen).  The trio won Oscars for their work on the picture as did director Chazelle and star Emma Stone.  And, in what is now a famous snafu, the 2016 film was really close to winning Best Picture.  

In the film, Stone is Mia, an aspiring actress who finds love with Sebastian, a jazz musician, played by Ryan Gosling.  While the film certainly has amassed its critics over the years, La La Land remains, to me, a beautiful testament to music and love, lost and found.  I can still watch this one over and over and will continue to smile my way through ‘A Lovely Night’ every time.  

A man stands in front of a couple

Cr. COURTESY OF Summit

Chicago

Roxie Hart may be one of the most iconic Broadway characters, with this musical being ever popular since its debut in 1975.  Played by Renée Zellweger in the movie adaptation, Roxie Hart is a dancer who longs for fame, only to find it in the most unexpected place.  The film also stars Catherine Zeta-Jones, Richard Gere, Queen Latifah, and John C. Reilly.  All of the stars earned Oscar nominations, with Zeta-Jones winning her category.  The 2002 film also won Best Picture. 

Chicago is ‘all that jazz’ with its music perfectly encapsulating the 1920’s era.  It’s an impressive song and dance spectacle that has a lot of humour considering its two main characters are awaiting their respective murder trials.   It also has a little something in common with Kiss of the Spider Woman.  Chicago’s screenplay was adapted by Bill Condon, who directs the new movie musical.  As well the two musicals share composers with John Kander and Fred Ebb.  I can easily say Chicago was one of their best, and the soundtrack to this film adaptation still holds up, even ‘Nowadays.’

Three people with makeup on their face

Cr. COURTESY OF Miramax

This post was written by
Hillary is a Toronto based writer, though her heart often lives in her former home of London, England. She has loved movies for as long as she can remember, though it was seeing Jurassic Park as a kid that really made it a passion. She has been writing about film since 2010 logging plenty of reviews and interviews since then, especially around festival season. She has previously covered the London Film Festival, TIFF (where she can often be found frantically running between venues) and most recently Sundance (from her couch). She is a member of the Online Association of Female Film Critics. When she’s not watching films or writing about them, she can be found at her day job as a veterinarian. Critic and vet is an odd combination, but it sure is a great conversation starter at an interview or festival!
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