What are you supposed to be?

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"Can't you guys tell? I'm the rapping paper!"

During Halloween, the characters dress up in costumes, in which they often engage in Halloween-related activities. Many of these costumes are icons or celebrities, most of which were popular/created the 1970s, '80s, and '90s, leaving most of the other characters unable to identify who a particular character is supposed to be dressed as.

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

Occurrences

Sketchbook (museum)

The last image offered ten dollars to anyone who can identify all of the costumes. They have all since been identified.

Homestarloween Party

Homestar Runner thought Strong Bad was the Chiquita Banana Lady, when Strong Bad was really Carmen Miranda (although the Chiquita Banana Lady's appearance was intentionally based on Miranda's).

The House That Gave Sucky Treats

Homestar thought Strong Bad was the Spanish Inquisition, and it is implied he thought Strong Bad was Cab Calloway and Strong Bad Wearing a Yellow Turtleneck, when Strong Bad was really Carmen Sandiego.

Pumpkin Carve-nival

Marzipan doesn't know The King of Town is Mario from the long-running, well-known video game series by Nintendo. This could be because Marzipan insists she doesn't play video games, as said in the same toon.
Strong Bad, who was in a Homestar Runner costume, said he thought The Goblin (in a Strong Bad costume) was the Green Hornet. Strong Bad then thought The Goblin was a Witches' Brew, while he was actually The Bee.
Homestar thought The Cheat was Witch's Brew when The Cheat was Russell.

3 Times Halloween Funjob

Homestar thought Strong Bad was El Debarge, Bubs thought he was Miami Sound Machine, Coach Z thought he was Terence Trent D'Arby, and he himself almost said he was Carmen Miranda again, while he was actually Ozone from Breakin'.
Homestar thought Coach Z was Wesley Snakes, when in fact he was Kool Moe Dee from The Treacherous Three.
Homestar couldn't identify what Bubs's costume was, calling it a "dirty man outfit", when Bubs was dressed as Mel Sharples, the owner of Mel's Diner in the movie Alice Doesn't Live Here Anymore and the TV show it spawned, Alice. Vic Tayback played the role.

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 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 he was some sort of a golf cart. He was actually Carl Spackler from Caddyshack.
Homestar thought The Cheat was a pile of leaves. The Cheat was actually Sigmund, from Sigmund and the Sea Monsters.
Coach Z thought Pom Pom was Big Boi from Outkast. Pom Pom was actually Big Boy, the mascot for the restaurant chain "Bob's Big Boy".

Halloween Potion-ma-jig

Homestar, seeing Strong Sad's Devo member costume, comments on it, saying, "Nice fire hydrant costume."
Homestar thought Strong Bad was Blanche from The Golden Girls. Bubs thought he was Phyllis Diller. Coach Z thought he was supposed to be his hot mom. The King of Town couldn't recognize his costume at all. Strong Bad was dressed as Jambi the genie, from Pee-Wee's Playhouse.
Homestar also thought Bubs was Lando Calrissian. He was actually the master of disaster, Apollo Creed from Rocky and Rocky II.
Strong Bad thought Pom Pom's costume, which was of Walter Sobchak from The Big Lebowski, was of "every guy at a truck stop."

TrogdorCon '97

Homestar asked Strong Bad to guess who he is supposed to be, to which Strong Bad answers successfully with very little effort.

Happy Hallow-day

Homestar remarked to Marzipan that he likes her "I have a caterpillar crawling across my forehead" costume. Marzipan was dressed up as Frida Kahlo.
When Homestar sees Strong Bad's Father Guido Sarducci costume, he thinks it is an evil Carmen Sandiego costume. Incidentally, Strong Bad did dress up as Carmen Sandiego five years earlier.
Strong Bad teases Strong Sad asking him if his costume was Strong Sad at his 20-year high school reunion. Strong Sad was actually Tony Clifton.

Decemberween Short Shorts

The Homestar ornament thinks the Strong Bad ornament is dressed up as a rhinestone cowboy. However, it isn't even Halloween.

Jibblies 2

Homestar mistakes Bubs for Schnieder from One Day at a Time',' The King of Town mistakes him for Monroe from Too Close for Comfort, and Marzipan can't figure out his costume at all. Bubs was really Ross from You Can't Do That on Television.
Homestar mistakes The King of Town for a melted Don King. The King was actually Al Sharpton.

Fan Costumes '07

Homestar thinks one of the photos is a picture of Marzipan, when it is actually of someone dressed as The Yello Dello.

yes, wrestling

In an Easter egg, Homestar thinks Strong Bad (dressed as his "il Cartographer" wrestling persona) is dressed up as Rudy from Fat Albert.

Costume Commercial

In an Easter egg, Coach Z is dressed as Marzipan, but he thinks he is dressed as himself.

Most in the Graveyard

Homestar confuses his own costume for Carrot Top, then turns around and "corrects" himself as being Crocodile Dundee. He was actually Yahoo Serious (ly).
Homestar confuses Strong Sad's Sam Kinison costume for one of Ma Fratelli from The Goonies.

Doomy Tales of the Macabre Teaser

As everyone stands silhouetted, Homestar thinks everyone is dressed in "covered-all-black-ink costumes", and accuses everyone of stealing his idea.

Doomy Tales of the Macabre

Speaking very quickly, Homestar identifies Pom Pom as "the underwater orange juice man" (he's a Pooka from Dig Dug), Strong Bad as the Scarecrow and Mrs. King (he's the Skull Kid from The Legend of Zelda: Majora's Mask), The Cheat as "the thorax" (he's actually The Lorax), asks Coach Z if he stole Mickey Mouse's pants (he's MC Skat Kat), and claims Marzipan is "off-duty Ronald McDonald" (she's Lola from Run Lola Run).

Which Ween Costumes?

Strong Bad correctly guesses that Bubs is dressed as a character from Die Hard, but says that he is a "Die Hard costume man", to Bubs' consternation.
Pom Pom is dressed as a snowglobe with all the characters inside him, but Homestar thinks he is dressed as a "last episode of St. Elsewhere".
Strong Sad is dressed as Ralphie Parker, but Strong Bad thinks he is dressed as a deranged Easter Bunny, while Homestar thinks he is Donnie Darko.
The King of Town is dressed as the Heat Miser, but Homestar thinks he is dressed as a "Devil Don King".
No one knows what exactly Coach Z is dressed as, so Strong Bad decides to ask. Coach Z says he is dressed as "rapping paper" and demonstrates with a rap, to everyone's annoyance.

I Killed Pom Pom

Homestar guesses that Coach Z is dressed up as a tube of "Evil Aquafresh". Coach Z is actually dressed as the mascot for hip-hop group A Tribe Called Quest.
Homestar thinks that Strong Bad is dressed as Jay Leno. Strong Bad is actually dressed as McDonald's Mascot Mac Tonight.
Homestar mistakes Strong Mad for a M.U.S.C.L.E. toy. He is actually Goro from the Mortal Kombat series.
Pom Pom is dressed as Homer Simpson as portrayed in the episode King-Size Homer. Homestar mistakes him for Dom Deluise.

The House That Gave Sucky Tricks

Homestar thinks that Strong Bad is dressed as "tropical Beetlejuice". He's dressed as Diamond Dave.
Homestar appears to have the general idea of Pom Pom's costume (Wilson from Cast Away), but cannot remember his name, guessing Franklin, Spaulding, and John Voight.
Homestar confuses Marzipan's Michael Jackson costume with her Prince costume from Jibblies 2.

Later That Night...

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@StrongBadActual

November 22, 2016 — Strong Bad exclaims that he is not dressed as "Evil Thomas Jefferson" or "Colonial Ice T" but as "Lin-Manuel Freakin' Miranda".

Haunted Photo Booth