From Homestar Runner Wiki
Smoking is one of the occasional vices indulged in by the Homestar Runner crew.
 The Cheat's Smoking
The Cheat is a smoker. While he usually smokes cigarettes, he also smokes the occasional old-style pipe. He normally smokes Trophy Lights cigarettes, usually after a period of stress or fatigue. Though sometimes his friends will try to get him to stop smoking, their attempts are never too successful. The Trophy Lights have been seen in a locker in Coach Z's locker room, where The Cheat reportedly sleeps sometimes.
- The Cheat's Smoking Challenge — The player must help The Cheat quit with nicotine gum.
- Where's The Cheat? — Strong Bad finds a pack of Trophy Lights in The Cheat's locker, which violates his New Year's resolution.
- Email big white face — A pixelated drawing of The Cheat shows him holding a smoking pipe.
- Email montage — The Cheat can be seen smoking after a day of door-to-door selling with the Wagon Fulla Pancakes. Marzipan is surprised that he smokes in the secret commentary for montage.
- Hairstyle Runner — One of the pictures in the gallery features Homestar smoking.
- Meet Marshie — "Pinner" has a cigar in the pile of marshmallows (this also appears as an Easter egg in island).
- Pigs on Head — Hank and Frank are both smoking cigars.
- Email fingers — Strong Bad has a lit cigar on his left hand.
- That A Ghost — Fat Dudley smokes a cigar.
- Teen Girl Squad Issue 8 — Cheerleader had a bowler derby hat, sunglasses, a mustache, a tie, and a cigar.
- Strong Bad and The Cheat's Store Thank You Message — Strong Bad lights a cigar with a burning pile of money.
- Email lady...ing — Strong Bad tries to smoke a cigar, but it explodes in his face.
- Email pop-up — Bubs is smoking a cigar in the Easter egg.
- Weekly Sketchbook — The Sneak is holding a cigar in one of the images.
- Email your funeral — In an Easter egg, Strong Sad is seen holding a cigar. In another Easter egg, future versions of Pom Pom and Strong Sad are smoking cigars.
- Dangeresque 3: The Criminal Projective — A cigar can be seen sitting in the ashtray on the desk in the Smoky Office during the game introduction, but by the time the game proper starts, it appears to have changed to a cigarette.
- Thorax Corporation — Leg Delabor's page has an animated GIF that at one point shows a lit cigarette.
- The Interview — the Smoky Office has an ashtray with a lit cigarette in it.
- The Smoky Office has also been seen with the lit cigarette many other times.
- 3 Times Halloween Funjob — Homsar appears dressed as Slash in an Easter Egg with a cigarette in his mouth.
- Teen Girl Squad Issue 5 — The Ugly One sticks her head in the ground, where her lungs proceed to fill up with sand and cigarette butts.
- Peasant's Quest Preview — the Videlectrix Mascot holds a cigarette while leaning on the Videlectrix logo.
- This is also seen in Peasant's Quest Animatic.
- Puppets on the Road — In Homestar and Craig's film "Staple-Down Life", the first two lines are "Smoking. Cigarettes."
- Teen Girl Squad Issue 10 — the party scene is introduced by a man smoking a cigarette with "AT THE PARTY" imprinted on it.
- Email space program — the filmstrip announcer wonders why Ted Averill isn't enjoying a "smooth, relaxing cigarette".
- Happy Hallow-day — At the end, Strong Bad is seen holding a cigarette.
- Email mini-golf — All Homestar finds in the Blue Family Recreation Water are cigarette butts and a bra.
- Limozeen vs. Sloshy — After learning that their flying tour bus doesn't have any shields, a member of sloshy asks if they have any cigarettes. The bassist hands him a box of them as their van is destroyed by Limozeen's hot lixx.
- Fan Costumes '07 — The 5th picture shown is of a man in a Strong Sad costume holding a cigarette. Strong Bad implies that, since everything is "spot on", that Strong Sad is a smoker.
- Email environment — Strong Bad's New Year's Resolution is to start watering Marzipan's flowers with recycled cigarette butts.
- DNA Evidence — Strong Bad has an ashtray with a lit cigarette in it.
- Hremail 7 — Melonade flavor Butt 1 features a crushed out cigarette on the can.
- Scroll Button Songs — In one of the songs, Coach Z raps, "And if you're tryin' to fade me then ya must smoke crack!"
- Email pizzaz — The Strong Bad dressed like a ship's captain is holding a corncob pipe.
- Commandos in the Classroom — Teachers are advised to "catch a nap or have a smoke" during the slide show. Later on in the show, the Blue Laser Commander tempts Firebert by asking if he wants to "smoke some candy."
- Email myths & legends — Strong Bad's "fence drawings" show a man smoking a pipe.
- Teen Girl Squad Issue 11— So and So asks for some "smokes".
- Sketchbooks — One image shows a representation of Strong Bad with a large mustache, smoking a pipe.
- A Death-Defying Decemberween — Homestar holds a pipe throughout his televised Decemberween special.
- Career Day — Strong Bad dressed up as Space Captainface says that his educational film will give the teacher enough time for a smoke break.
- On Break — While in his Tragic Clown Dog costume, Strong Bad takes a smoking break, but actually smokes a white crayon.