The Simpsons: 10 Utterly Heart-Breaking Moments You'll Never Forget

4. Lisa And The Whale

It often feels like Lisa Simpson is trapped in a perpetual loop of disappointing revelations: she is an idealist, which is pretty much the worst thing to be in Springfield, since cynicism and snark will out, and she is thus forced to face harsh truths at almost every turn.

It is through Lisa's eyes that we've explored bullying most profoundly, and social acceptance, and issues of self-image, and it is through her eyes that we've seen the most profoundly engaging portraits of lost love and lost life. In terms of love, we'll come to that, but the issue of heart-breaking death comes in the episode "The Squirt And The Whale," when Lisa is treated to the devastating realisation that no matter how strong her will, or the force of her idealistic convictions, sometimes life is harsh.

When Bluella the whale washes up on Springfield beach, Lisa fantasises about saving her, but on her inevitable death Lisa is understandably distraught, and overcome with a sense of hopelessness. Despite her best efforts and convictions, she was unable to do something positive for the whale, or her children, and you can't ignore the allegorical implications that come with that helplessness, and feel like Lisa is being forever set up for a life of disappointment and false dawns.