What are you supposed to be?

From Homestar Runner Wiki

No, I'm Carmen freakin' Mir—no, wait. I'm Ozone. From Breakin'.

What are you supposed to be?
In the Halloween toons, the characters dress up in costumes in which to go 'trick or treating'. A lot of these costumes are icons or celebrities from the 80s' and 90s', leaving most of the characters unable to identify who a particular character is supposed to be.

This is put quite frankly by The King of Town in Halloween Potion-ma-jig where he says: I wish you'd dress up as something I could recognize! Pop culture... mumble grumble!

Occurrences

Homestarloween Party

• Homestar thought Strong Bad was the Chiquita Banana lady, while in actuality, he was Carmen Miranda.

The House That Gave Sucky Treats

• Homestar thought that Strong Bad was the Spanish Inquisition, Cab Calloway or Strong Bad Wearing a Yellow Turtleneck, while in actuality he was Carmen Sandiego.

Pumpkin Carve-nival

• Marzipan doesn't know that The King of Town is Mario from the Nintendo game Super Mario Bros because she doesn't play video games.
• Strong Bad, who was in a Homestar costume, thought that The Goblin, in a Strong Bad costume, was a green hornet. Strong Bad then thought that The Goblin was a Witches' Brew, while he was actually The Bee.
• Homestar thought The Cheat was Witches' Brew, while in actuality, he was Russell.

3 Times Halloween Funjob

• Homestar thought Strong Bad wa El Debarge, Bubs thought he was Miami Sound Machine, while Coach Z thought he was Terence Trent D'arby, he was actually Ozone from Breakin'.
• Homestar thought Coach Z was Wesley Snakes, when in fact he was Kool Moe Dee from The Treacherous 3.

Halloween Fairstival

• Strong Bad asked Bubs, "So, Bubs, your approach this year was to ensure that absolutely no one recognized your costume?" Bubs was dressed up as One of the 3 Most Important People in the World, from Bill & Ted's Excellent Adventure.
• Homestar was confused about his own costume. He thought that he was some sort of a golf cart. He was actually Carl Spackler.
• Homestar thought The Cheat was a pile of leaves. He was actually Sigmund, from Sigmund and the Sea Monsters.

Halloween Potion-ma-jig

• Homestar thought that Strong Bad was Blanche from The Golden Girls. Bubs thought that he was Phyllis Diller. Coach Z thought he was supposed to be his hot mom. The King of Town didn't recognize the costume either. Strong Bad was dressed up as Jambi the genie, from Pee-Wee's Playhouse.
• Homestar thought that Bubs was Lando Calrissian. He was actually the master of disaster, Apollo Creed from Rocky I & II.