“Hopeless Bleak Despair” is another They Might Be Giants song that takes on the depressing/saddening subject matter with upbeat/happy sounding music. Appearing on the group’s eighth album Mink Car in 2001, John Linnell sings from the perspective of a person burdened by this ‘hopeless bleak despair’.

Placed between “Yeh Yeh” and “Drink!“, two tracks where John Flansburgh sings about the joys of having a good time with a girlfriend and drinking respectively, “Hopeless Bleak Despair”, sung by John Linnell, is something of a sobering listen. The narrator’s life falls apart because of this despair. His family leave him, and he is fired from his job. It isn’t until the final verse where it is revealed, amongst angelic background choir vocals, that the narrator is dead – how he died is not said but we can assume it’s suicide – and was finally separated from it. However, the narrator goes to hell while the despair ‘ascends to heaven’ so even then it gains the upper hand.

The song’s quite funny that way. After everything that has happened to him whilst alive, the narrator can’t catch a break even in the afterlife. You want to feel sorry for him but Linnell’s enthusiastic vocals and the forceful performance by the band pushes those feelings aside, and instead will have you singing along to this poor person’s problems.