H*R.com Halloween '09 - "Doomy Tales of the Macabre"

I don't know about Homestar's, but Strong Sad's costume was the blocky 3D moving man from the 80's music video to Dire Straits' "Money for Nothing," a staple from the early days of MTV. Marzipan was dressed at the titular main character from the movie Run Lola Run.
 
Nailed:
Coach Z
The Cheat
Homsar
Pom Pom (though it took me a bit)

Kicked myself for missing:
Marzipan (we watched that movie in a film class I took)

The Zelda characters went over my head.

I think the question we should be asking is, how does Strong Bad type WITHOUT boxing gloves on?
 
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