Strong Sad is an interesting example of character evolution.
In his early appearances, he was a total downer, both depressed and depressing, whose only major contributions to his friends' escapades include boring the legendary Yello Dello to sleep with his thinly-disguised life story1, helping Coach Z with his problems pronouncing the word "job"2, and being constantly victimized by Strong Bad, Strong Mad, and/or The Cheat. He'd often say stuff like "Each day, we die a little more" or "I dream of my own death. Over and over and over...", often ruining social gatherings (like Homestar's party in the first Halloween cartoon3) with his sheer depressingness.
However, as the Homestar Runner website grew, so did Strong Sad grow as a character. He became less and less of a punching bag for his brothers, though Strong Bad still thinks he's a loser and still harasses him whenever possible. He gained some personality traits besides being a depressing Goth type guy: we've learned he likes to play board games with The Cheat and Homsar4, his favorite band is The Cure, and he has a bit of a crush on Marzipan. He also gained enough confidence to occasionally deflate Strong Bad's ego with a snide comment or choice piece of sarcasm. He's even made a contribution to the arts by co-directing a video for the song Experimental Film by They Might Be Giants5. Strong Sad's also demonstrated a bit of a vindictive streak, from taking the opportunity to taser Strong Bad in episode 3 of Strong Bad's Cool Game For Attractive People to imagining various darkly humorous ways for his friends to meet their doom when they snubbed him one Hallowen.6
But much like that other round-headed born loser, Charlie Brown, Strong Sad still gets the worst of it quite often.
- "In Search of the Yello Dello"- http://www.homestarrunner.com/yellodellomenu.html
- "A Jorb Well Done"- http://www.homestarrunner.com/cantsayjob.html
- "Homestarloweeen Party"- http://www.homestarrunner.com/homestarloween.html
- "Where's The Cheat?"- http://www.homestarrunner.com/whereis.html
- "Experimental Film"- http://www.homestarrunner.com/expfilm.html
- "Doomy Tales of the Macabre"- http://www.homestarrunner.com/ween09.html