Cross-dressing

From Homestar Runner Wiki

Cross-dressing is when a male or female dress up as their opposite gender. This has occurred many times in the Homestar Runner universe, especially on Halloween.

Appearances

• Pom Pom, Too — Pom Pom is seen dressed as the Statue of Liberty in one scene.
• Homestarloween Party — Strong Bad's costume is of Carmen Miranda.
• 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.
• Email different town — If he were to make the town different, Strong Bad would envision Homsar as a modestly hot girl, only for it to not turn out as well as planned (on account of his broken imagination).
• 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.
• 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.
• More Fan Costumes — The last picture is of a girl wearing a Homestar costume.
• 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".
• 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.
• 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 — Coash Z wears hairculers and acts like a housewife when he hears Bubs is going on a date with Marzipan.

Screenshots of Cross-dressing

Representing freedom in Free Country, USA	Carmen FREAKIN' Sandiego	"Hey, ho. Let's go."	Bob Rossipan
"I'm forever your girl."	"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!"
FAIRY'D	"I can be a teen girl."	Little Strong Riding Bad	"Meep."
"So confused. HOT Homestar?!?"	"Now you children skee-daddle."	Cara Carabowditbowdit	Just one almond based sweet delight
"I call them soolnds!"	"Hey, whatcha doing there, sista!"	"You WORT?!"