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

5. Barney's Award-Winning Film

When the Springfield Film Festival comes to town, Barney Gumble wows the audience and judges with his unfortunately named short film "Pukahontas," which shows rare self-awareness from the alcoholic fool.

Heavily referencing the events of The Lost Weekend, and owing a lot stylistically to Koyaanisqatsi, the film shows how aware of his condition, and the likely result of it Barney actually is. As the haunting refrain of "Un Bel di Vedremo," from the opera Madama Butterfly by Giacomo Puccini soars, Barney is transformed from bumbling fool to a tragic figure, trapped and fully aware that he will likely die.

The last line: "Don't cry for me, I'm already dead" is the icing on the cake, giving a heart-breaking moment to a traditionally comical character, and marking Barney with pathos for the rest of the show's run. Of course the comic pay-off somewhat derails the emotional impact of the moment, but on its own terms, the short is beautiful and haunting and adds a massive note to Barney as a character.