Cross-dressing

From Homestar Runner Wiki

"Could you reach the jar of 'Old Lady Rub' for me? 'Cause I'm an old lady."

Dressing as girls (also known as "being in drag") occurs many times in the Homestar Runner universe.

Appearences

• Homestarloween Party — Strong Bad's costume is of Carmen Miranda.
• The House That Gave Sucky Treats — Strong Bad's costume is of Carmen Sandiego.
• Email different town — Homsar is turned into a girl, but his male voice remains.
• Shopping for Danger — Fightgar dresses as an old lady to get some info from Blue Laser.
• 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.
• Main Page 22: Strong Bad appears with Marzipan's ponytail.
• 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 Dressing as girls

FAIRY'D	"I can be a teen girl."	Cara Carabowditbowdit	Just one almond based sweet delight
The Chiquita Banana lady	Carmen FREAKIN' SanDiego	Modestly hot my eye!	Little Strong Riding Bad
Things have started getting "crazy-go nuts"