Musicals can’t always be fun. In fact, in doing research for this article, I’ve noticed that a lot of them are just plain tragic. From fresh takes on actual Greek tragedies (Hadestown) to modern messages on mental health (Next to Normal), there’s enough musicals to create at least ten lists of this nature. But which songs will worm their way into your ears while simultaneously punching you in the gut? Get ready to find out.
In order to keep certain productions from sweeping the list, I’m limiting entries to one song per show. I’m also only including songs from musicals I’ve seen, so there’ll be no Les Miserables or Hamilton present. Sorry hardcore Broadway fans, maybe next time. With all that out of the way, here are, in no particular order, some of the saddest musical songs of all time:
1. “All You Wanna Do”- SIX: The Musical
Combining pop stars with Henry VIII’s wives, SIX is jam-packed with sassy remarks and memorable songs. However, it also highlights how Henry mistreated his wives. For example, Katherine Howard, Henry’s fifth wife, was groomed, sexually abused, and then beheaded. She was believed to have been around nineteen years old at the time of her death.
Howard’s song, “All You Wanna Do,” is particularly effective at masking her trauma with jokes before hitting the audience with the reality of all the horrors she had to endure. The first two verses are fun, sexy, and snarky. You can even hear the audience laughing along. That is, until the third verse, where both Howard and the audience begin to realize how she’s been exploited. By the time the fourth chorus ends, Howard is in tears and the audience sits in shell-shocked silence. The climax of her breakdown is an absolute gut punch, especially since it points out the audience’s complacency in enjoying her exploitation for entertainment. Samantha Pauly and Jodie Steele’s versions are particularly impactful, with both of their physical performances adding to Howard’s emotional anguish. It’s a powerful song that gets more tragic with each listen and one of my personal favorites.
2. “She Used to Be Mine”- Waitress
There’s a reason Waitress was Tony and Grammy-nominated.
The story follows Jenna, the titular waitress and expert pie baker, whose life is turned upside down when she becomes pregnant. She begins hiding money to enter a pie contest, hoping to win and use the prize money to leave her abusive husband, Earl, and start a new life. But when Earl finds and takes the money, a distraught Jenna breaks down, lamenting her circumstances.
“She Used to Be Mine” is the honest outpouring of a woman at her lowest point. It encapsulates all of her fear, anger, and regret, desperate for a second chance that seems just out of reach. The song’s delivery is so raw, making Jenna’s pain palpable. It’s heartbreakingly beautiful and definitely a must-listen for any disappointed dreamers.
3. “Goodbye Until Tomorrow/I Could Never Rescue You”- The Last Five Years
A mashup counts as one song, right? Eh, doesn’t matter. My list, my rules.
One of the most interesting things about this production is its timeline. Examining the dissolution of Cathy and Jamie’s marriage, we alternate between the lovers’ perspectives, with Cathy traveling backwards in time while Jamie travels forwards.
This mash-up is the musical’s finale, with an optimistic Cathy singing about how she’s been waiting for Jamie her entire life. Simultaneously, future Jamie is sitting in the pair’s apartment penning his good-bye letter and officially ending their relationship. There’s something so heart-breaking at witnessing the contrast between Cathy’s hopefulness and Jamie’s resignation, at the different intentions behind their good-byes. The Last Five Years is my second favorite musical, just behind SIX, and the strength of its songs is a major reason why.
4. “Requiem”- Dear Evan Hansen
Say what you want about its plot, but Dear Evan Hansen’s creators know how to pen a sad song. Most people would cite “Words Fail” and “So Big/So Small” as its biggest tear-jerkers, but “Requiem” is so quietly tragic. After Connor Murphy’s suicide, his sister Zoe and father Larry can’t bring themselves to mourn his loss. The former resents Connor for how poorly he treated her, while the latter believes that he didn’t appreciate the privileged life he was given. Meanwhile, Connor and Zoe’s mother, Cynthia, is ecstatic to learn that Connor had a friend, with this new hope preventing her from fully mourning the tragedy of his loss.
It’s a devastating feeling when you’re unable to fully grieve a family member after they’ve passed, to feel angry and resentful at the deceased instead. Similarly to the previous entry, the contrasting emotions of the characters combined with similar lyrics packs an emotional punch despite its soft delivery.
5. “Lifeboat”- Heathers: The Musical
I’ll admit, I wasn’t a fan of “Lifeboat” the first time I heard it, but it’s grown on me quite a bit since then.
Heathers isn’t afraid to point out high-school hypocrisy and the dangers of dismissing teenage problems. And while the musical does delve into pretty dark territory, it makes some very good points regarding teenage cruelty and the dismissal of mental health issues. After Heather McNamara’s friends are murdered and their deaths are staged as suicides, she attends a televised therapy session. There, she reveals the constant social pressure she’s under and her own struggle with suicidal thoughts.
McNamara is the most empathetic Heather by far, and hearing her admit that everyone around her is willing to dispose of her to get ahead hits particularly hard. The song perfectly encapsulates the fragility of both McNamara’s popularity and her mental health. It’s made even more heart-breaking when her classmates’ accusatory reactions drive her to attempt suicide. Her predictions proved true, and had Veronica not intervened, Heathers’s body count would’ve been one higher. At a time when suicide is the second-leading cause of death for children ages 10-14 and the third-leading cause for ages 15-25, this song hits just a bit too close to home.
6. “Alabanza”- In the Heights
After the matriarch of the barrio, Abuela Claudia, passes away, the entire neighborhood comes together to mourn her loss.
Both the musical and the film have this song perfectly placed in their respective timelines. The musical has the news of Abuela Claudia’s death interrupt the celebratory “Carnaval del Barrio” and follows it up with Nina’s grief-stricken “Everything I Know.” The film switches up the order, preceding “Alabanza” with “Paciencia y Fe,” which recounts Abuela Claudia’s life story before having her move on. Regardless of which version you prefer, watching the barrio come together in their grief is a beautifully melancholic image.
7. “How Could I Ever Forget?”- Next to Normal
If I wasn’t limiting entries, Next to Normal would take up the majority of this list.
Diana suffers from bipolar disorder and depression and is haunted by the hallucination of her son Gabe, who she sees as a teenager despite him having died as an infant. After electroconvulsive therapy causes her to forget Gabe’s death, her husband, Dan, is reluctant to remind her. But when Diana finds out, the pair relive the night Gabe died.
This song is absolutely heart-breaking, especially for anyone who’s ever lost a child. While this marks Diana’s return to grief, it’s the double-meaning for Dan that truly broke me. He lost his wife alongside his son. That night changed their relationship forever, and he’s been fighting his entire life to try and get it back. The song ultimately serves as the catalyst for Diana’s road to recovery, as she finally begins to admit the reality of her situation and her desire for closure. But, man, does it tug our heartstrings before we get a hint of happiness.
8. “Flowers”- Hadestown
You can’t expect a musical based on the story of Orpheus and Eurydice to end well.
Seeking safety and security, Eurydice signs a contract to become a worker in the Underworld, leaving her lover, Orpheus, behind. However, once she gets to Hadestown, she realizes the gravity of her situation. She’s condemned herself to become a forgotten worker, forever laboring the town with no chance of returning to the surface. Regretful of her choices, she dreams of life on the surface and the lover she’s left behind.
The song becomes even more heart-wrenching when you remember how Eurydice’s story ends. Orpheus is granted permission to rescue her as long as he doesn’t look back to make sure she is following. But doubt comes in, and he turns back just as she’s reached the exit, condemning her to return to Hadestown, this time for good. Having her dream of returning to the surface, to flowers and life, rescinded just as it’s within her grasp, is about as devastating as you can get.