Film

Merrily We Roll Along

Stephen Sondheim's musical about ambition and friendship, told backwards from Hollywood success to Broadway youth. Paul Mescal and Ben Platt anchor a film that moves in reverse, each scene a step closer to the moment everything felt possible. It's both funny and quietly devastating—a story about the choices that remake us, told in the order we'd rather not remember them.

Should you watch it?

Watch it if you hold a soft spot for musicals about friendships that curdle, and you enjoy a sharp, bittersweet tone where wit and regret share the same song.

Skip it if you want a brisk plot or a light mood; this is talky and wistful, and its ambitions and disappointments build slowly rather than sprinting toward anything.

What it asks of you: Patient attention for a long stretch, since the timeline runs backwards and you must keep rebuilding the characters as they were, not as they became.

If you liked this

tick, tick... BOOM!2021

A musical about an artist at a crossroads, wrestling with ambition and time running out. Directed by Lin-Manuel Miranda with raw emotional honesty and genuine stakes about creative compromise.

But The film is essentially three people in small spaces. Long stretches feel like watching someone work through anxiety rather than traditional entertainment.

tick, tick... BOOM! poster

The Producers2005

A musical comedy about show business corruption and friendship tested by success. Nathan Lane and Matthew Broderick are genuinely hilarious, and it shares Merrily's dark humor about what ambition costs.

But The tone whipsaws between broad farce and genuine pathos. Some find it tonal chaos; others find that's the point.

The Producers poster

Mulholland Drive2001

A non-linear film about Hollywood dreams and how they remake us. Haunting, structurally bold, and explores the psychological cost of ambition with genuine dread. Essential viewing for anyone interested in how films tell backwards stories.

But It's deliberately cryptic and demands active interpretation. Three-hour runtime with a narrative that explicitly resists closure.

Mulholland Drive poster

Not sure tonight? Get a pick in a minute, starting from Merrily We Roll Along

The wildcard

Something you would not have found on your own.

Boyhood2014

Both stories move through time as their narrative engine. Merrily goes backward and compresses decades into two hours; Boyhood moves forward in real time. Both ask: how did we get here?

A twelve-year film shot over a decade, following a boy and his family through ordinary moments. No story arc, no dramatic turns—just the slow accumulation of becoming yourself. By the end, you've lived twelve years of his life.

But Nothing happens. There's no structure except time itself. If you need clear narrative propulsion, this will feel like watching paint dry.

Boyhood poster
More like this (5)

Cabaret1972

A musical about a group of friends in a decaying world, where performance and reality become impossible to separate. Every frame is carefully composed; the songs are devastating.

But It's relentlessly dark. There's no sentimentality and almost no relief. The pleasure is entirely in the artistry, not the story.

Cabaret poster

The Last Five Years2014

Jason Robert Brown's musical about a marriage told in two simultaneous timelines—one forward, one backward. Like Merrily, it uses unconventional structure to excavate what we miss about the people we lose.

But One character sings forward in time, one backward. It's structurally challenging and occasionally feels gimmicky rather than earned.

The Last Five Years poster

Sweet Charity1969

A musical about a woman chasing happiness through relationships and ambition in New York. It's got Shirley MacLaine at her most vulnerable, and the score is Cy Coleman at his best.

But The film is visually arch in ways that work against genuine emotion. Some scenes feel like they're mocking the character rather than understanding her.

Sweet Charity poster

A Chorus Line1985

A musical about artists at an audition, each one revealing their own version of ambition and compromise. The choreography is extraordinary and the songs are efficient storytelling.

But It's essentially a series of monologues set to song. There's no plot and the emotional register is one note, however well-executed.

A Chorus Line poster

The Umbrellas of Cherbourg1964

Like Merrily, it's a musical about the moment everything changes, told with Sondheim-level sophistication about what compromise means. Both understand that ambition and love are almost always incompatible, and both refuse to forgive the choice.

A French musical where a young couple in love must choose between love and ambition. Shot in candy-colored perfection, the songs are melancholy, and it ends with a gut-punch of a final scene. It's beautiful and it will destroy you.

But It's in French with subtitles. The melodrama is sincere and unironic—if that register makes you uncomfortable, the film won't work. Also, it's *sad*.

The Umbrellas of Cherbourg poster

People

Cast

Directing

Production

Recommended by