Strong Bad Wearing a Shirt
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- A Jumping Jack Contest — Strong Bad wears a shirt as part of his Pom Pom costume.
- The House That Gave Sucky Treats — Strong Bad wears a turtleneck sweater and a trenchcoat as part of his Carmen Sandiego costume.
- Email impression — Strong Bad wears a grey "PHYS ED" sweater as part of his Strong Sad costume.
- 3 Times Halloween Funjob — Strong Bad wears a red tanktop as part of his Ozone costume.
- Halloween Fairstival — Strong Bad wears a green shirt and a purple jacket as part of his Joker costume.
- Email hygiene — Strong Bad wears a shirt as part of his Gene costume.
- Email original —Strong Bad wears a lederhosen for one costume, and a Mountie shirt for another.
- Jibblies 2 — Strong Bad wears the suit that Beetlejuice wears as part of his costume.
 Work Shirts
- Email other days — Strong Bad wears a Micro Palace polo shirt.
- Biz Cas Fri 1, Biz Cas Fri 2, Biz Cas Fri 3, email 4 branches, and email from work — Strong Bad wears a polo shirt.
- Email stand-up — Lil' Strong Bad wore a T-shirt for his comedy act.
- The Secrets That I Keep — Lil' Strong Bad wears a shirt in the picture with Little Strong Sad.
- Email origins — Lil' Strong Bad wears a T-shirt with a truck on it.
- Email the chair — Lil' Strong Bad wears a gray sweatshirt.
- Email the paper — In one of Strong Bad's flashbacks, Lil' Strong Bad wears an "evil" duckie shirt.
- Homestar Quiz — Strong Bad wears a suit and red tie as CGNU principal.
- A Mother's Day Message — Strong Bad wears a blue sailor's outfit.
- Email lures & jigs — Strong Bad is wearing a shirt at The Pond.
- Email ghosts — Strong Bad wears a Ghostbusters shirt.
- Everybody to the Limit — Strong Bad wore a shirt that said "To the Limit!".
- Decemberween Email Menu — Strong Bad wears a blue sweater in the Decemberween card Easter egg.
- Email different town — Strong Bad wears a loose blue shirt when singing about Homsar.
- Email rampage — Strong Bad wears a suit during his legal rampage.
- Email modeling — Strong Bad wears a turtleneck sweater, a business suit, and a turquoise sweater with a scarf.
- Email technology — Strong Bad wears a lab coat.
- Email secret identity — Strong Bad wears a dirty white undershirt as Vance Mudgeman.
- In the original draft for flashback, Strong Bad was supposed to wear Homestar's Star shirt, but when Marzipan gave Homestar the same one to replace his duckie shirt, Strong Bad ripped off his shirt.
- Email keep cool — Although Strong Bad is not actually seen wearing one, his tan lines seem to imply he has been wearing a tank top for some time during the summer.
- Email concert — Strong Bad wears a sloshy T-shirt.
- Email nightlife — Strong Bad wears a skyblue shirt.
- Happy Dethemberween — Strong Bad is wearing a holiday sweater and, as it appears, a shirt underneath. At one point, he also appears to be wearing the lab coat from technology.
- Trogday 08 — Strong Bad is wearing a French red and white striped shirt.
- Strong Bad Gameways — Strong Bad wears a stewardess shirt.
- Email love poems — Strong Bad wears a black turtleneck.
- Strong Bad's Cool Game for Attractive People — Shirts are included in the outfits you can wear in the game.
- Email magic trick — Strong Bad wears a shirt as a flowy-sleeved moneygician and as a street magician.