Strong Sad Smiling

"Hold on!"

As his name implies, Strong Sad is rarely happy. However, from time to time, primarily in toons from 2007 and later, he manages to crack a smile.

Appearances

Strong Sad's Secret Styles — Strong Sad smiles in a video clip showing a young Strong Bad giving him a noogie.
Email labor day — When he makes the joke about Strong Bad's invitation being DELETED, he cracks the tiniest of smiles.
Email extra plug — He smiles as he watches a picture of Andy Griffith's head taped to the TV with Strong Mad and The Cheat in the basement.
Email radio — He smiles involuntarily while under his radio persona.
Bug In Mouth Disease — He smiles a bit after Strong Bad suggests he try "putting stuff in quotes" in his search for The Blue Ones.
Email record book — He gives a big grin for his picture in Strong Bad's book.
A Folky Tale — Strong Sad grins slightly after he fools Coach Z into thinking he was dead.
Happy Hallow-day — He smiles involuntarily because of excess sunlight.
Email looking old — Strong Sad smiles widely when while talking to a "lace-lifted" Strong Bad, whom he refers to and treats as his great grandmother.
DNA Evidence — He laughs maniacally about how the world will never know the truth about the DNA evidence.
Ever and More — He smiles after he begins "believ[ing] in the message".
Email concert — He smiles when mocking Strong Bad's outfit, and after entering the room when Strong Bad is telling Homestar Runner about sloshy.
Email pizza joint — He smiles as he reviews The Pizz in Review Revue.
Email nightlife — He smiles after explaining to Marzipan how he spends his time at Club Technochocolate not dancing.
Somber Vacation — Strong Sad smiles in a picture of him holding his favorite tropical beverage and also in a postcard from Depressio Beach.
Most in the Graveyard — Strong Sad smiles when he wonders if he has "willed [himself] to death".
Coach Z's 110% — Strong Sad smiles as the narrator speaks.
Kick-A-Ball — Strong Sad smiles when he gets picked.
79 Seconds Left — Strong Sad smiles when he pours water on his knee.
Email hremail 3184 — Strong Sad smiles while describing the things he will do "with a vengeance".
Email imaginary — Lil' Strong Sad smiles while playing with Scotty Titi.
Compy Catalog — Strong Sad smiles while singing his song about the mail arriving.
Email independent — Strong Sad smiles when talking about his film school degree, and also after mentioning Art's House.
Doomy Tales of the Macabre — Strong Sad smiles after all the characters come for a surprise party.
Store Other 2-D Stuff — One of the Decemberween cards portrays all three of the Brothers Strong, as well as The Cheat, smiling.
I Killed Pom Pom — Strong Sad smiles when he admits to his "secret shame slash finest hour".
sbemail 206 — Strong Sad smiles when he says, "Did someone say, 'nerd cultures'?"
The House That Gave Sucky Tricks — Strong Sad smiles as he asks about Large Bean plushies at "the museum gift shop". Strangely, when he smiles here, it is his normal mouth flipped upside down, instead of his usual smiling mouth animation. Because of this, it looks like he has an underbite, like Homestar Runner.
Homestar Runner Goes for the Gold — Strong Sad smiles when he becomes Strong Glad.
@StrongBadActual tweet (9 Aug 2017) — Strong Sad smiles after applying Fluffy Puff Marshmallows Nibbles So Near Medicated Patch.
Email too cool — Strong Sad smiles upon the realization he's become cursed for life by watching Senor Cardgage's character video.
Mr. Poofers Must Die — Strong Sad smiles while making jokes about Marzipan's costume.

Screenshots of Strong Sad Smiling

Ah, the (dumpy) memories..	"Maybe it got 'da-leet-ed'."	Andy Griffith!	RADIO'D!
Biggest Waste of Dump	"Oh, Boolean operators! 'Blue' and 'Ones'!"	"Somebody shoot me!"	"Yes, I saw your new hip! It looks great!"
"The world will never know for sure!"	"I really do!"	"Oh, hello, pleatèd boots."	"Slosh-ay!"
"...a price that won't leave a dent in your wallet!"	"And if I'm feeling really crazy, I'll actually get out on the dance floor, and bust some fresh not-dancing."	"Wish U were here!"	"I've finally willed myself to death!"
"Ooh, I think he picked me!"	"It tickles!"	"Nice reflexes, Scotty!"	"That was the happiest I've ever been..."
"...You all really do care!"	"I'm glad that I'm flying!"	"Finally!"	"It's fine, whatever's cool with me!"