Cross-dressing

From Homestar Runner Wiki

Cross-dressing is when a male or female dress up as their oppisite gender. This has occured many times in the Homestar Runner universe.

Appearences

• Isle of Pom: 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.
• Toons Menu — Marzipan dressed as Bob Ross from Joy of Painting.
• Email 2 emails: Coach Z pretends to be "Hot Girl #37" by putting on her nametag.
• Email different town: Strong Bad imagines that Homsar is a "modestly hot girl".
• Shopping for Danger — Fightgar dresses as an old lady to get some info from Blue Laser.
• Halloween Fairstival: Marzipan's costume is of Willy Nelson.
• Teen Girl Squad Issue 8: Cheerleader briefly appears with a moustace, tie, bowler hat and a cigar, making her look 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 portrait: Strong Bad pretends Lord Quackingstick is the mermaid, Princess Shell-bra, in his own self-portrait.
• 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".

Screenshots of Cross-dressing

Representing freedom in Free Country, USA	The Chiquita Banana lady	Carmen FREAKIN' SanDiego	"Hey, ho. Let's go."
Bob Rossipan	"Check it out! I'm Hot Girl Number 37!"	Modestly hot my eye!	"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 you's guys. The battle of the Bands!"	FAIRY'D	"I can be a teen girl."
Little Strong Riding Bad	"Meep."	Cara Carabowditbowdit	Just one almond based sweet delight