Cross-dressing

From Homestar Runner Wiki

Cross-dressing is when someone dresses up as a member of the opposite gender. In the Homestar Runner universe, this usually occurs on Halloween.

Appearances

• Pom Pom, Too — Pom Pom is seen dressed as the Statue of Liberty when he is being described as patriotic.
• Homestarloween Party — Strong Bad's costume is of Carmen Miranda.
• Tis True, Pom Pom, Tis True — Strong Sad is dressed as a nun when Homestar Runner imagines everyone as if they were in the Middle Ages.
• The House That Gave Sucky Treats — Strong Bad's costume is of Carmen Sandiego and Marzipan's costume is of Joey Ramone.
• TV Time Toons Menu — Marzipan dressed as Bob Ross from Joy of Painting.
• Shopping for Danger — Fightgar dresses as an old lady to get some info from Blue Laser.
• Halloween Fairstival — Marzipan's costume is of Willie Nelson.
• Teen Girl Squad Issue 8 — Cheerleader briefly appears with a mustache, tie, bowler hat and a cigar, making her look (somewhat) like a male.
• Email long pants — Homestar wears Daisy Dukes as an attempt to get "light globes".

• In the commentary, Homestar claims that he does not wear Marzipan's skirts anymore.

• HomestarRunner.com PAY PLUS! — In the Teen Girl Squad sample, the Arrow'd Guy is dressed as a female fairy.
• Teen Girl Squad Issue 9 — Mr. Pitters dresses as Cheerleader in hopes of being a "teen girl".
• Grumblecakes (video) — Strong Bad is dressed as Little Red Riding Hood in one scene.
• Halloween Potion-ma-jig — Marzipan's costume is of Beaker.
• Email highschool — Homestar is seen (from the knees down) dressed as a nanny in the middle school flashback.
• Email secret identity — Strong Bad dresses in a long, brown wig when he writes as his secret female identity, Cara Carabowditbowdit.
• Email senior prom — Strong Bad wears a tiara when he is elected Prom "Queen".
• Email retirement — Strong Sad dresses up as a bearded lady in "Strong Bad's Amazing Feats of Wonder".
• Happy Hallow-day — Coach Z's costume is of Queen Latifah.
• Date Nite — Coach Z wears hair curlers and acts like a housewife when he hears Bubs is going on a date with Marzipan.
• Email more armies — Strong Mad wears basketballs as fake breasts while portraying Tito's beautiful assistant.
• Jibblies 2 — Marzipan is dressed as the pop singer Prince.
• Email fan club — Strong Sad forces Strong Bad to wear a bonnet while writing slash fan fiction about him and Homestar.
• Email licensed — Strong Bad appears as a princess on the cover for "The Secret Princess and Her Oppressive Authority Figure 4".
• Somber Vacation — Strong Sad gets a burn that leaves an unaffected area in the shape of a bikini top. However, he claims that this is a skin condition and that he can't help how he tans.
• Email your edge — The Cheat wears a pink and white apron while he and Strong Bad pretend to be grandmas baking.
• Strong Bad's Cool Game for Attractive People — The Cara Carabowditbowdit wig appears as a costume item.
• Strong Badia the Free — Strong Bad claims to be haunted by nightmares of a "milkmaid Homestar".
• Costume Commercial — Coach Z is wearing a Marzipan-themed swimsuit in an Easter Egg.
• Baddest of the Bands — The Cheat wears a bikini while posing for the album cover Strong Bad sends Limozeen.
• Most in the Graveyard — Marzipan is dressed as Stevie Ray Vaughan and The King of Town is dressed as Hello Kitty.
• Dangeresque 3: The Criminal Projective — The Poopsmith plays a girl who got kidnapped by a heartless monster.
• 8-Bit is Enough — In Peasantry, Strong Sad is seen wearing a princess hat, but he thinks he is a wizard.

Screenshots of Cross-dressing

Representing freedom in Free Country, USA	Carmen FREAKIN' Sandiego	"Hey, ho. Let's go."	Bob Rossipan
"Could you reach the jar of 'Old Lady Rub' for me? 'Cause I'm an old lady."	"Now try harmonizing with the butternut squash."	"No yous guys. The Battle of the Bands!"	"Creepy pants all the time get some!"
FAIRY'D	"I can be a teen girl."	Little Strong Riding Bad	"Meep."
"Now you children skee-daddle."	Cara Carabowditbowdit	"Just one almond paste filled sweet delight!"	"I call them soolnds!"
"Hey, whatcha doing there, sista?"	"You WORT?!"	A little lopsided	"I think you missed a little bit when you were shaving."
"...giving Homestar a deep-tissue massage."	Secret Princess Strong Bad	"This is just how I tan!"	"Take that thing off!"
"This Coach Z Coustume is spot on!"	"Lucky for me, Marzipan isn't the only blonde in town..."	"It's really starting to concern me that you keep dressing up as dudes."	"I dressed up as my favorite candy."
"But you're a beautiful woman now!"	"Just look at my wizard hat!"

See Also

• Gender Confusion