Simple Plan - "How Could This Happen to Me"
That tune about the perils of drunk driving became the go-to joke for the 2000s Internet. Any flash cartoon or YTMND that focused on "Emo" played that melodramatic number as crude mockery. It transcended its original, painfully sincere purpose and instantly became a parody of itself. Most bad songs transform into memes years later, but Simple Plan received immediate ridicule. Unfortunately, what started as unintentional comedy devolved a rapidly exhausted joke that was thankfully put down by the the close of the decade.
Plain White Ts - "Hey There, Delilah"
Is the man's woman 60? I strain to think of a single woman under the age of 40 who has that name. It's painfully tryhard emotionalism is further compounded by the whiny vocals which function as a sonic weapon. It's astonishing that man's voice hasn't sparked a wave of violent crimes.
Vanessa Carlton - "A Thousand Miles"
"A Thousand Miles" should be my jam on paper—melancholy piano hook, wistful lyrics, early-2000s sincerity but there's something about how overproduced and melodramatic it is that turns it into a white wine spritzer of a song: sugary, cloying, and pretending to be deeper than it is. It's the soundtrack to a montage of a sad rich girl staring out a car window.
Fountains of Wayne - "Stacy's Mom"
Everyone who likes this song is a douchebag.