From the bittersweet melody of heartbreak to the comic relief of dark humor, funny sad songs have been a staple of popular music for decades. They are the tunes that make us laugh through our tears, beckoning us to join in and sing along with each melancholic lyric.


These songs have a unique ability to connect us to our shared humanity, providing us with solace and understanding in moments of sadness and struggle.


So, sit back, grab a tissue, and get ready to experience the perfect combination of humor and heartbreak with these funny sad songs.




“Everybody Hurts” – R.E.M


This ditty by a well-known alternative rock band explores the theme of sadness in a tongue-in-cheek style. It strikes an unusual balance between humor and seriousness, with lyrics urging listeners to hold on and recognize that everyone experiences tough times. Despite the melancholic tone, the song features an upbeat tempo and catchy melody that make it hard to resist tapping your feet.


Overall, it’s the perfect choice for those who want to feel a mix of emotions and maybe even have a laugh despite the tears.




“Tears in Heaven” – Eric Clapton


This Eric Clapton classic tackles the heartbreak of losing a child and somehow finds a way to seamlessly weave wit and humor into its emotional lyrics. The track is a beautiful and melancholic tribute that finds its brilliance in the way it explores the unique mix of emotions that arise when dealing with death.


It’s a somber track that still manages to become a light-hearted and humorous anthem that anyone who has ever lost someone can relate to.




“Mad World” – Gary Jules


So, there’s this song that’s like, funny and weirdly sad at the same damn time, you know? It’s called “Mad World” and it’s by Gary Jules. The lyrics are pretty simple, but like, they hit you in a way that you’re like, “wait, what?”. The whole vibe of the song is super melancholic, and the way he sings it is just hauntingly beautiful.


It’s like, you listen to it and you feel a sense of longing and emptiness, but also like, a weird comfort in that feeling. It’s a whole-ass vibe, man.




“Hallelujah” – Jeff Buckley


This hilarious and heart-wrenching song tells the story of love lost and the ensuing sadness. With poetic lyrics and an emotive vocal performance, it’s difficult not to burst out laughing and burst into tears at the same time. The poignant and melancholic melody is beautifully paired with the song’s funny lyrics, resulting in a uniquely moving listening experience.




“Fast Car” – Tracy Chapman


Tracy Chapman’s “Fast Car” is a humorous yet melancholy song about a dead-end life and the dreams that keep the protagonist going. The song expresses complex emotions, blending a sense of longing for a better life with an acceptance of the hardships of the present. The instrumentation adds to the melancholic tone, featuring sparse acoustic guitar chords and a hauntingly beautiful melody.


Overall, “Fast Car” is a unique and powerful song that captures the bittersweet nature of human existence.




“The A Team” – Ed Sheeran


Alright, challenge accepted. So, there’s this track that I came across the other day that’s kind of a weird, mixed-bag deal. It’s got a real upbeat sound to it, bouncin’ bassline and plinky guitar riff and everything, but the lyrics are pretty dark, to say the least. I mean, it’s all about this girl he met who’s got a pretty grim little life story.


I guess it’s one of those funny-sad songs, you know? Like, catchy as hell but with this undercurrent of misery running through it. Definitely not something for a sunny day, that’s for sure.




“The Freshmen” – The Verve Pipe


“The Freshmen” by The Verve Pipe is a puzzlingly poignant composition in which the complicated emotions of heartbreak, regret, and nostalgia are woven together with raw lyricism and a haunting chorus. The song effortlessly captures the confusing feelings of being young, in love, and facing unexpected consequences, making it a perfect fit for the theme of funny-sad songs that evoke both laughter and tears.


The Verve Pipe delivers their signature sound with melancholic guitar riffs, emotive vocals, and lyrical depth that is both introspective and relatable.




“How to Save a Life” – The Fray


The Fray’s “How to Save a Life” is a deeply moving track that managed to become one of the most highly acclaimed emotional ballads of the 2000s. Although the song has been featured in various films and TV shows, including “Grey’s Anatomy,” “Scrubs” and “One Tree Hill,” it’s important to remember the complexity of its message.


With a mix of soaring vocals, poignant lyrics, and a haunting piano melody, the song manages to capture a sense of both melancholy and hope, inspiring listeners to confront their fears and anxieties head-on, regardless of how difficult and daunting they may seem.




“Brick” – Ben Folds Five


So, there’s this tune called ‘Brick’ by Ben Folds Five. It’s a tricky little number – kinda upbeat and jazzy but with some really intense and emotionally raw lyrics. The funny thing is that the music almost seems to undercut the depth of the words – it’s like a sad clown or something.


But if you listen close, you’ll hear some pretty gut-wrenching lines about a couple going through an abortion. It’s a bit of a mind-bender, not gonna lie.




“I Will Remember You” – Sarah McLachlan


Now, picture this – a funny sad song to summon your innermost emotions. Paired with the haunting voice of Sarah McLachlan, “I Will Remember You” makes for a unique contrast where the melody is sad yet stirring. It is perfect if you’re feeling inexplicably and strangely happy, alongside a sense of melancholy that refuses to win over the fun mood.


With lyrics that are deep, but not heavy, it’s a perfect addition to create an ovation in the company of friends.




“The Sound of Silence” – Simon & Garfunkel


Yo, have you checked out that Simon & Garfunkel tune about silence, man? It’s like this crazy funny sad song that’ll make you feel all sorts of things at once. The lyrics are so perplexing, like, they make you think about the meaning of life and stuff.


And the way they sing it, it’s so bursty, like it’s building up to something, you know? But then it just fades away into nothingness, and that’s like the saddest part of it all. Definitely check it out, dude.




“Yesterday” – The Beatles


Now, something that should actually make you laugh amidst all the sadness. Beatles’ classic “Yesterday”, a tune that might appear as a melancholic ballad yet packs a lighthearted and comic punch. With its catchy melody and Paul McCartney’s unique voice, it tells a story of someone losing a lover, their house, and a previously proclaimed belief in themselves that everything would get better with time.


It creates a mischievous twist that you almost don’t see coming, but once it hits you, it’s hard not to at least have a little chuckle.




“Skinny Love” – Bon Iver


This track from Bon Iver is a total heart-wrencher. It’s a beautiful song with melancholic lyrics and a haunting melody that captures the raw emotions of a person going through a tough time. The lyrics are poetic and introspective, with a sense of hopelessness and vulnerability that make it a perfect fit for any playlist about funny sad songs.


It’s a song that’s full of contradictions and surprises, and it will leave you with a sense of emptiness and longing.




“Wake Me Up When September Ends” – Green Day


Oh man, the fourteenth song on this list is such a hilarious bummer. Green Day’s “Wake Me Up When September Ends” manages to be both uproariously funny and depressingly sad. Billie Joe Armstrong’s signature gritty vocals pair perfectly with the song’s melancholic melody to create a tune that you can’t help but sing along to, even as it brings you down.


It’s the kind of song that makes you want to laugh and cry at the same time, a real rollercoaster of emotions.




“The Drugs Don’t Work” – The Verve


“The Drugs Don’t Work” by The Verve is a candid and thought-provoking ode to the impact of drug addiction on our lives. The melody and the lyrics may seem grim at first glance, but they create a compelling narrative that reflects the fragile and fleeting nature of our existence.


It’s a poignant and sobering reminder of the cost of addiction, but also a cathartic and emotionally charged song that can resonate with anyone who has experienced loss or struggle in their life.




“Nothing Compares 2 U” – Sinead O’Connor


This track by Sinead O’Connor touches on the melancholic and comedic aspects of heartbreak. O’Connor’s smooth synthesizers and unique voice highlight the sadness of losing someone while pointing out some ludicrous aspects of the ways people cope. Whether you’re feeling heartbroken, contemplative, or just a little bit quirky, “Nothing Compares 2 U” is the perfect tune to get you through.




“The Night We Met” – Lord Huron


“The Night We Met” by Lord Huron is an introspective and melancholic song that’ll make you shed a tear or two, yet the dreamy harmonies in the melody result in a slightly uplifting tone. It’s a funny sad song that offers a unique balance between the somber and the hopeful, making it a fascinating and perplexing musical experience.


The lyrics are simple and repetitive, which allows the listener to focus on the emotion conveyed by the artist’s distinctively young but wise-sounding voice. Don’t be surprised if you find yourself both laughing and crying at the same time after listening to this contemporary masterpiece.




“Dancing On My Own” – Robyn


“Dancing On My Own” by Robyn is a perfect example of a funny sad song. With its upbeat and energetic melody, one might not initially detect the underlying sense of heartache and loneliness that permeates throughout the lyrics. But upon closer inspection, the irony behind the juxtaposition of the joyous instrumentals with the melancholic lyrics is striking.


The song encapsulates the aching feeling of being in love with someone who is in love with someone else, while also acknowledging the catharsis that can come from just letting go and dancing on one’s own.