Bear Holding a Shark
From Homestar Runner Wiki
The bear holding a shark is actually one of Strong Badia's "security counter-measures", as Strong Bad puts it; whenever The Cheat touches the Tire, the bear holding a shark pops up after an electric shock from the tire. For reasons that are never really explained, The Cheat seems to have a strong phobia of bears holding sharks. The Bear-Shark also plays the part of "headhunters" on Strong Bad's Riverquest Safariventure. It is "scared off" by firing a starting pistol in its general direction twice.
It has been featured in a documentary detailing its roots in Strong Badian lore. The myth/legend originated as a British distance runner holding a fish with a 'fro wig, and supposedly through years of bad storytelling and the telephone game, evolved into the Bear-Shark we know today. Apparently, Homestar and his "dog" Pom Pom were walking in the woods when they saw (and caught footage of) the "very scary monsterm'n", who suspiciously had white feet with blue soles. Strong Sad did not believe the myth/legend very much, and dismissed the bear holding a shark as either a weather balloon or a foreign exchange student.
In Fan Costumes '06, two young women (referred to as "Ho-ties" by Strong Bad) are shown. One of them wears the Bear Holding a Shark t-shirt, with a frown on her face, while the other one is actually dressed as the bear holding a shark, with a full head bear mask, bear arms, and is holding a stuffed shark over her head. Strong Bad remarks, "I like the upgrade to Bear holding a Tiger Shark... Or was that just like... the only shark they had left at the aquarium gift shop?" The Cheat is not scared of this Bear Holding a Shark.
The Bear holding a Shark has a small part in Dangeresque 3: The Criminal Projective as the Western Lowland Grizzlysharkasaurusbot holding a shark. When traveling to Strong Borneo, it is activated by Dangeresque and Renaldo, but it stopped with the Nunchuk Gun. It was burninated along with the rest of Strong Badia in 8-Bit Is Enough, but was still left in one piece.