20 of the Saddest Musical Songs of All Time

The saddest sad songs from musicals

Everyone loves a good cry every now and then and these musical theatre numbers are sure to get the tears following.

Prepare tissues for our rundown of some of the saddest songs from musicals.

I’ll Cover You (Reprise) – Rent

This song will never not leave you in tears.


Words Fail and So Big, So Small – Dear Evan Hansen

Act two of Dear Evan Hansen is a real tear-jerker thanks this pairing of songs back to back.


It’s Quiet Uptown – Hamilton

There’s a lot of moments in Hamilton that will make you cry but this number hits the hardest.


The I Love You Song – 25th Annual Putnam County Spelling Bee

This wildly fanciful song is simultaneously beautiful and devastating.


With You – Ghost

This song hits especially hard when performed by Cassie Levy.


She Used To Be Mine – Waitress

This act two, 11’o’clock number marks an emotional turning point for lead character Jenna.


Somewhere – West Side Story

This gorgeous Bernstein and Sondheim number is an all time classic with good reason.

All of Les Misérables

The title says it all, really.


It’s Hard to Speak My Heart – Parade

Jason Robert Brown’s score for Parade has no shortage of devastating numbers. Coming at the of act one, It’s Hard to Speak My Heart is an incredibly heartfelt number.


He’s Not Here – Next To Normal

Next To Normal won that Pulitzer Prize for Drama for a reason.


Something’s Missing – Come From Away

These lyrics will break your heart.


I’ll Be Here – Ordinary Days

This number from Off-Broadway show Ordinary Days sees a woman reminisce about the loss of her husband in the September 11 attacks.


What Would I Do? – Falsettos

This penultimate song from Falsettos is sure to have you in tears.


Everything I Know – In The Heights

Nina reminisces about Abuela Claudia in this emotional act two number.

My House – Matilda The Musical

Performed by Miss Honey in the second act, this gorgeous song by Tim Minchin is severely underrated.


Burn – Hamilton

Eliza Hamilton’s heartbreak and anger are palpable in this powerful song.


No One Is Alone – Into the Woods

This song offers solace and wisdom in the face of tragedy, a hallmark of Stephen Sondheim’s work.


Memory – Cats

Grizabella’s yearning for her past glory days is captured in this hauntingly beautiful song.


Road To Hell (Reprise) – Hadestown

As Hermes sings, “It’s a sad song, but we sing it anyway.”


Finishing the Hat – Sunday in the Park with George

George’s artistic obsession and isolation are explored in this emotionally charged song


About the author: Rachel Wise

UK based freelancer journalist Rachel contributes regularly to Stageberry with features and interviews from the hottest new shows and stage stars.


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