- Ed's reaction to Brandy cutting him off from the team in the episode The Big Game.
- Pretty much any moment that makes Ed into a Woobie qualifies as this.
- Rip Van Whiskers. Well, Whiskers is revealed to have not touched any poison after all so it all ended out fine, but it's still pretty depressing nonetheless.
- Brandy hurting Mr. Whiskers' feelings in "Believe in the Bunny".
- Brandy's actually quite sad breakdown when she discovers she's not a purebred dog, with her giving up on not just primping but taking care of herself in general.
http://tvtropes.org/pmwiki/pmwiki.php/TearJerker/BrandyAndMrWhiskers
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