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59 Broadway Songs That Will Devastate You

There's a pain goes on and on.

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NOTE: To avoid oversaturating this list with too many songs from the same shows, I limited my choices to one song per musical. The songs are presented in semi-random order, not ranked. Tissues are needed for all.

1. "You'll Never Walk Alone" (Carousel)

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Sure, this is a song of hope, but like most songs of hope, it's sung in a moment of utter despair. And it won't bring Billy back.

2. "Losing My Mind" (Follies)

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Nothing breaks your heart like unrequited love. Scratch that — nothing breaks your heart like Sondheim writing about unrequited love.

3. "Till We Reach That Day" (Ragtime)

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You'll start crying the moment Brian Stokes Mitchell lets out that anguished scream. (But you'll probably already be crying, because Ragtime.)

4. "I'll Cover You (Reprise)" (Rent)

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Listen, any musical with a funeral scene is going to ruin you. That's just the way it is.

5. "Sunrise, Sunset" (Fiddler on the Roof)

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And so will weddings.

6. "What Would I Do?" (Falsettos)

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No one captures the rage and devastation of grief like William Finn, and the closing number from Falsettos is particularly brutal.

7. "This Nearly Was Mine" (South Pacific)

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This song doesn't always bring the tears, but there's something about this particular performance. Oh, let's face it, Brian Stokes Mitchell could sing literally anything and it would make you weep.

8. "Flying Away (Finale)" (Fun Home)

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The finale of Fun Home probably works better in context, but its emotional power is unmatched.

9. "Around the World" (Grey Gardens)

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There are two kinds of people in this world: those who view Little Edie as the tragic figure she is, and literal monsters. Your reaction to this song is an important litmus test.

10. "Somewhere" (West Side Story)

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Spoiler alert: Things do not end well for Tony and Maria.

11. "Some Things Are Meant to Be" (Little Women)

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Spoiler alert: Things do not end well for Beth.

12. "Gethsemane" (Jesus Christ Superstar)

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Spoiler alert: Things do not end well for Jesus.

13. "Not a Day Goes By" (Merrily We Roll Along)

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Another Sondheim song about heartbreak. Don't act surprised. Just listen and feel things.

14. "Alabanza" (In the Heights)

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More grief, this time from the great Lin-Manuel Miranda. (Note: Hamilton would be represented on this list if the OBCR were out already.)

15. "There Will Be a Miracle" (See What I Wanna See)

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A somewhat more obscure show, but a gorgeous, tear-inducing number all the same.

16. "Maybe This Time" (Cabaret)

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"Maybe this time I'll be lucky." (You won't.) "Maybe this time he'll stay." (Nope.)

17. "Memory" (Cats)

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Ignore the fact that she's a cat, and focus on the pain. Nobody does it like Betty Buckley.

18. "There Is a Fountain/It Don't Make Sense" (Parade)

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Another funeral song from another show that has plenty of heartwrenching moments. It's the first appearance of Jason Robert Brown on this list, but rest assured there will be several more.

19. "What I Did for Love" (A Chorus Line)

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"Look, my eyes are dry." LIAR.

20. "Lily's Eyes" (The Secret Garden)

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One brother singing about the woman he loved and lost, the other singing about the woman he loved who never loved him back. It's sad on every level.

21. "Move On" (Sunday in the Park With George)

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Sondheim. Bernadette. Mandy. And the feeling. AND THE LIFE.

22. "Something Wonderful" (The King & I)

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Is there anything more tragic than trying to find the good in your asshole husband? Poor Lady Thiang.

23. "I'm Here" (The Color Purple)

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The best performance of the best song from The Color Purple. Fantasia is unbelievable. The sheer power of her voice can extract tears from the coldest of hearts.

24. "Wicked Little Town" (Hedwig and the Angry Inch)

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The Hedwig version and the Tommy Gnosis version are devastating in different ways. Pick your poison!

25. "Not While I'm Around" (Sweeney Todd: The Demon Barber of Fleet Street)

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Theoretically this song should be comforting. Instead, it's deeply upsetting.

26. "Fifty Percent" (Ballroom)

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Another devastating song about the pain of settling.

27. "I Am the One (Reprise)" (Next to Normal)

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Honestly, all of Act 2 of this show is sob-inducing. But this fucking song. "Hi, Dad." Bye.

28. "Bill" (Show Boat)

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By itself, this might sound like a sweet (albeit honest) love song. In the context of the show — and everything Julie endures — it's incredibly emotional.

29. "Being Alive" (Company)

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"But alone is alone, not alive." Ugh.

30. "Pretty Funny" (Dogfight)

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Pasek and Paul: the new generation of composers making us feel things.

31. "Bare" (Bare: A Pop Opera)

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It's a love song, yes, but you can probably guess how this ends.

32. "Last Night of the World" (Miss Saigon)

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Once again: It's a love song, yes, but you can probably guess how this ends.

33. "How It Ends" (Big Fish)

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OK, here's how it ends — Edward dies. And yes, he lives on in his stories, but it's not the same. Let it out.

34. "The Party's Over" (Bells Are Ringing)

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A classic that still resonates, because broken hearts never go out of style.

35. "Stars and the Moon" (Songs for a New World)

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It's funny. It's sweet. And then, because it's Audra McDonald singing Jason Robert Brown, it creeps up on you and suddenly why is my face wet.

36. "Proud of Your Boy" (Aladdin)

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Scoff all you want: This is the most gorgeous song in Aladdin, and it should never have been cut from the film. Do not think about Howard Ashman while listening to this or you may never recover.

37. "A House Is Not a Home" (Promises, Promises)

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It's not all "Turkey Lurkey Time" for Fran, OK?

38. "For Good" (Wicked)

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And while we're on the subject of Kristin Chenoweth, even Wicked detractors get a little misty-eyed when Elphaba and Glinda part ways.

39. "Love Who You Love" (A Man of No Importance)

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As if this song weren't emotional enough, it's performed by the late Roger Rees, which makes it that much more devastating.

40. "Music Still Plays On" (A New Brain)

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Even though A New Brain ends on a positive note, there's plenty of trauma throughout — particularly when Roger's mother is sure he's never going to wake up.

41. "Left Behind" (Spring Awakening)

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Put that single tear away, Jonathan Groff. It's too much to bear.

42. "Always Better" (The Bridges of Madison County)

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Yes, yet another tragic love story. This song speaks to Francesca's lack of regret, but that doesn't make it any less upsetting. And the combination of Jason Robert Brown and Kelli O'Hara is pretty incredible.

43. "The Hill" (Once)

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"Falling Slowly" gets all the attention, but let's not overlook the quiet despair of "The Hill."

44. "The Light in the Piazza" (The Light in the Piazza)

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This is such an overwhelmingly beautiful show that the entire score can make you cry. Here's a great example!

45. "Epilogue: In Every Age (Reprise)/Finale" (Titanic)

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Spoiler alert: Things do not end well for the Titanic.

46. "The Flesh Failures/Let the Sunshine In" (Hair)

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The '60s are over and Claude is dead. Enough said.

47. "I'll Be Here" (Ordinary Days)

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Another fairly obscure show. Another Audra McDonald rendition of a song about a relationship. Another barrage of feelings.

48. "I Will Never Leave You" (Side Show)

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Not sure which is more tragic — the lives of Daisy and Violet, or the fact that Side Show didn't last longer on Broadway.

49. "Nobody Needs to Know" (The Last Five Years)

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Trying to pick a tear-jerking song from The Last Five Years is like shooting fish in a barrel (of tears). They're all devastating. This is one of the worst offenders.

50. "Epilogue - Valjean's Death" (Les Misérables)

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Once again, all of Act 2 qualifies for inclusion here. And Act 1, for that matter. As Marius sings in "Empty Chairs at Empty Tables," "there's a pain goes on and on." (He was definitely talking about Les Misérables.)

51. "The I Love You Song" (The 25th Annual Putnam County Spelling Bee)

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The fucked-up thing about this song is that it occurs in the middle of a mostly very funny show. And then suddenly, Olive is pouring her heart out. And the tears are flowing, because William Finn.

52. "Middle Spaces" (The Fortress of Solitude)

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This show never really got its due — such a gorgeous score with incredible performances. There are plenty of moments to cry at, but if you're dry-eyed during the finale, there might be something wrong with you.

53. "Why" (Tick, Tick... Boom!)

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Jonathan Larson's lesser known show might not have the emotional impact of Rent, but "Why" is heartbreaking, especially given Larson's untimely death just as he was on the cusp of truly breaking through as a composer.

54. "Home" (The Wiz)

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How exciting that NBC is airing The Wiz live this year! We can all cry in unison.

55. "Time Heals Everything" (Mack and Mabel)

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Mack and Mabel was a major failure at the time, perhaps because it's so relentlessly depressing. "Time Heals Everything" is yet another song about staying hopeful — those are always the hardest.

56. "As If We Never Said Goodbye" (Sunset Boulevard)

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Norma Desmond might think she's getting her big comeback — but she isn't. And therein lies the tragedy of this song.

57. "No One Is Alone" (Into the Woods)

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"I wish." "I know." I cry.

58. "Anytime (I Am There)" (Elegies: A Song Cycle)

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It's a William Finn song from a show called Elegies. That alone should tell you where this is headed.

59. "Send in the Clowns" (A Little Night Music)

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Bernadette singing what may be Sondheim's most iconic song — with Sondheim on the piano — is very powerful. But frankly, all great versions of this song are just as emotionally draining. And what better way to end this cryfest.

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