Some folks will tell you that the saddest instrument in the world is perhaps the Spanish guitar, but I know better: the saddest instrument in the world is the thrift-store synthesizer. As Exhibit A, I present you with "Tonight Was A Disaster," by Casiotone for the Painfully Alone, the solo project of Californian depressive Owen Ashworth. The instrumental bridge that commences right at the track's midpoint is probably the most plaintive forty seconds 2001 has to offer; pathetic in a classical sense.
As a bonus, I'll throw in "Number Ten," a song which concludes with a uniquely heartfelt usage of searing circuit-bent noise. It sounds pretty much like a dental drill banging around inside a washing machine, and yet it's also unmistakably the sound that rages in your skull when you're in the middle of having your heart broken.