Airdate: Sunday, December 4, 2005
Sender: Dylan Bragers (aka Coolio da Fabio), Texas
After an aborted attempt at doing a musical e-mail, Strong Bad answers a question from Dylan Bragers, AKA Cooli da Fabio ("No one calls you Coolio da Fabio, AKA Quit Makin' Up Nicknames For Yourself!") asking if he's ever considered having a portrait commissioned of himself.
Strong Bad also considers having a picture of himself done in the style of the black-and-white ink portraits seen in "rich guy newspapers", the sort that look like they're made out of Morse code ("Dah dah dah dee dee dee... I a-am ho-o-olding a real-ly ol-d cel-l-l pho-o-one."), or a black velvet portrait of himself hunting skunks, to be showcased "in only the finest double-wide trailers" alongside moose lamps and blacklight posters of unicorns on snowmobiles.
The Cheat is still taking his sweet time on a hand-sculpted (or rather, mouth-gnawed) wooden sculpture of Strong Bad, while the best Strong Mad can manage is a glitter-coated macaroni painting. Strong Bad decides it's time for a self-portrait... in the form of a cheap photo cut-out of a muscular version of himself with a "keyswordtar" and a hawk.
Strong Bad passes the time plotting his escape from the cut-out by chatting it up with Lord Quackingstick and Princess Shellbra (both played by a duck-head toy).
- Brick Joke: Strong Bad's first imaginary portrait (fine art painted by a "Deutsch Master") features him with a duck-head toy. At the end, Strong Bad actually owns that toy in reality, and he calls it Lord Quackingstick.
- Continuity Nod: During the spot with the velvet portrait of Strong Bad, after the moose lamp gets knocked over we hear Homestar mutter "Thanks for breaking my moose lamp", in a reference to "caper".
- Did You Get a New Haircut?: An Easter egg shows Strong Bad after he escaped from the cut-out. His head is still through the hole, but he broke that part off the rest of the portrait. Homestar's reaction?Homestar: Strong Bad, there's something different about you. Did you get a haircut?
- Help, I'm Stuck!: Strong Bad gets his neck stuck in the self-portrait cut-out, since the hole is far too small to fit his head through.
- Her Code Name Was "Mary Sue": As usual, Strong Bad's self-portrait is a ridiculously idealized version of himself: tall and muscular, with a sword-keytar on his belt, a falcon resting on his hand, and a mermaid at his 'electric boot-clad feet.
- Humongous Mecha: The Cheat spray-paints a "rad, rad robotank" over Strong Bad's first attempt at an imagined portrait.
- I Will Wait for You: Strong Mad shouts this in response to Strong Bad's line about going to jail for trying to get a kindergarten student to make macaroni art of him.
- Instrument of Murder: Parodied with the "keyswordtar" included in Strong Bad's "self-portrait"; it's half-sword, half keytar.
- Malicious Misnaming: After mocking Dylan for making up his own nickname, Strong Bad says "I'm just gonna call you Dealin' Burgers, which I assume doubles as an accurate job description."
- Mistaken for Pedophile: Discussed, Strong Bad complains to Strong Mad that he could go get an actual kindergartner to make a macaroni portrait of himself if he wanted, "Except that sounds pretty creepy and I'd probably go to jail."
- Musical Episode: Subverted. Strong Bad announces "It's a musical Strong Bad Email this week!" near the beginning, but gives up singing after a few seconds.
- Orphaned Punchline: From an Easter Egg featuring Strong Bad showing off his keyswordtar to Homestar: "...so that's when I realized I don't even need Lamaze classes."
- Overly Long Gag: The Cheat attempting to gnaw a wooden sculpture of Strong Bad.Strong Bad: You're really just... goin' to town there, aren't ya? (beat) I'm gonna leave you two alone.
- Seashell Bra: The mermaid from Strong Bad's final portrait wears one. He even names it Princess Shellbra.
- Unsound Effect: Strong Bad says "Whammy bar!" while showing off his "keyswordtaur" to Homestar.