The official unofficial band of TV Tropes has some awfully sad songs.
- "I've Got a Match," a soft, slow-moving, kinda upbeat tune about the catastrophic ending of a relationship between two very unhappy people.
- They have described "Destination Moon," as "about being really, really sick when you think you're not". And that puts it lightly, making the song's Unreliable Narrator a Woobie par excellence.
- "The End of the Tour". TMBG tunes tend to be open to interpretation, but many of the potential messages here are absolutely soulcrushing. The one that sticks out the most is "enjoy what we have because one day, it's gone", and more specifically, "one day we won't be partners anymore; we won't share that interest that binds us, anymore; we won't be friends anymore". Of note is this verse, which has spawned some harrowing alternative theories concerning everything from survivor's guilt to the loss of a loved one:Never to part since the day we met out on Interstate 91
I was bent metal, you were a flaming wreck, when we kissed at the overpass
I was sailing along with the people driving themselves to distraction inside me
Then came the knock on the door, which was odd, and the picture abruptly changed
- "No Answer," a Dial-A-Song exclusive. It's an absolutely devastating take on the topic of life cut short. The cherry on top comes in the final verses:On the southeast expressway where they found the empty stroller
Being blown by the traffic through the trash along the shoulder
Was it the ghost of somebody who decided not to begin
And under the sound of the car horn, can you hear a small voice asking
"What's it like to be alive?"
- "Sometimes A Lonely Way"'s lyrics plainly state a volley of awful truths. And, in a TMBG rarity, the music's every bit a downer as the lyrics.
- "They'll Need A Crane." It sounds upbeat, but once you hear the lyrics it becomes clear that, much like "I've Got a Match" the subject matter is couples in abject misery.
- In a strange way, "Ana Ng" could qualify, with the application of some Fridge Horror. The lyrics suggest it's about a man whose soulmate is someone he'll never meet, and yet the song is catchy and fun-sounding.
- "Doctor Worm", despite its silly start, quickly reveals itself to be about a musician that nobody takes seriously and is denied even his preferred name. There is clear Applicability in his story, especially his lonely Subdued Section near the end.
- "Drink" is a Drunken Song with a rather somber composition that can be easily interpreted as a story about an overworked man and his downfall into alcoholism.
- "My Man", which is sung from the point of view of a paralyzed body who is desperate to reconnect with the brain.
- "What Is Everyone Staring At?" (another Dial-A-Song exclusive that was later recycled into another song called Sleepwalkers), a song with a subject matter similar to the aforementioned "I've Got A Match" and "They'll Need A Crane", as the lyrics are about a couple who are desperately trying to deny that their relationship is falling apart despite it being blatantly obvious to everyone around them. It's especially sad if you yourself have been in this situation and the melancholy instrumentals don't help either.What is everyone staring at?
What is everyone looking at?
Haven't they seen
Two people in love?
What is everyone staring at?
Have I got something on my face?
Should I rub my hand
On the side of my mouth?
Did I forget to wash somewhere?
Can you please inspect my teeth?
- Their cover of "Caroline No", for the same reason as the original Beach Boys version. Flansburgh's singing and Linnell's accordion just drive it home.
- "Climbing the Walls." The title is even a euphemism for a stress-related breakdown.The deep end, the deep end
People talk a lot,
but they don't know.
They pretend, they pretend.
They don't really know how deep it goes.
- All Time What is a shockingly straightforward song for TMBG, told from the point of view of someone whose significant other left them. Its heartbreakingly realistic, especially to anyone whos gone through a difficult breakup.
- From the 2018 edition of Dial-A-Song (later released on My Murdered Remains), we have Best Regrets, a deeply melancholy song seemingly about regretting a past relationship or friendship (although as with nearly all TMBG songs, its a bit ambiguous). Even the music is heartbreaking!
- "The music video for "By the Time You Get This." While the hammy performance of the actors might be funny, the story of a husband trying to comfort his wife by covering up the windows so she doesn't have to watch the earth's imminent destruction via a fiery asteroid collision.