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 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.
- 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".
- 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 hairculers 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.
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!" |
 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?!" |
 A little lopsided |
 "I think you missed a little bit when you were shaving." |
