From Homestar Runner Wiki
One of Stinkoman's most defining phrases, though always variable, revolves around the prospect of challenges. The only actual challenges we ever see Stinkoman fight (aside from boss fights in Stinkoman 20X6) are challenges against The Homestar Runner and Sticklyman. While Stinkoman engages in both challenges and fighting, he typically only challenges actual opponents, whereas fighting is a much lesser form of combat. Despite this, he refers to the training regimen he has with Vector Strong Bad as a "challenge", perhaps because of the greater danger of "Level 2". It is considered a parallel to Strong Bad's overuse of the word competition.
- Email japanese cartoon — The theme song for Stinkoman K includes the word "Challenge" five times.
- 20X6 vs. 1936 —
- "I'm training for fighting, or maybe a challenge."
- "Are you asking for a CHALLEENGE?"
- Marzipan's Answering Machine Version 8.0 — "Can I interest you in a challenge? Or maybe some light fighting?"
- Under Construction —
- "Correct me if I'm wrong but are you asking for a challeeeeeeenge?!"
- "Diiid we miss a challenge?" (said by 1-Up)
- "The fighting was decent, but it wasn't much of a challenge."
- Email time capsule — "Some sort of a challenge buried in the GROOOUUND??"
- Stinkoman 20X6 —
- In the intro sequence, "STINKOMAN IS ALWAYS LOOKING FOR A FIGHTING OR A CHALLENGE"
- Whenever Stinkoman starts a boss fight, he asks "Are you asking for a challenge?"
- In the intro to level 1-1, "ARE YOU INQUIRING ABOUT A CHALLENGE??"
- In the intro to level 2-1, "I WILL FIND THE CHICKEN WHO'S BONE THIS IS AND ASK HIM IF HE IS ASKING FOR A CHALLENGE!!"
- In the intro to level 2-3, "ARE YOU ASKING FOR A CHALLENGE?"
- In the intro to level 4-3, "ARE YOU JOKING? YOU MUST BE JOKING! THIS HAS GOT TO BE SOME FORM OF JOKE CHALLENGE!" and "WHAT AN AMATEUR ATTEMPT AT ASKING ME FOR A CHALLENGE."
- After winning 5-3, "I FOUGHT MY VERY OWN CHALLENGE AND WON!!" (said by 1-Up)
- In the intro to level 6-3, "I HOPE THERE ARE MORE CLOUDS AND ELECTRIC PLUGS FOR ME TO CHALLENGE!"
- In the intro to level 7-1, "I'M GONNA CHALLENGE THE CRAP OUT OF THEM."
- After winning 8-3, "I MIGHT EVEN SAY HE WAS A NEGATIVE CHALLENGE!!"
- In the Level Select menu, the description for level 6 is "Recreational challenges on the token cloud level".
- Because, It's Midnite (karaoke) —
- "I'm gonna challenge ya!"
- "These guys look like they're challenging each other."
- "Are you asking for a karaoke challenge?!"
- Happy Trogday — "Is this your crazy, mixed-up way of asking me for some type of birthday challenge??"
- Email alternate universe — "Hey, guys! How's challenges?"
- Email web comics — "Sometimes I wish I could challenge my own self."
- Twenty THANXty Six — "Who would've thought that giving thanks was such a formidable challenge?" Additionally, the program the characters appear on is named "Stinkoman and the Challenge of the Crystal Shards".
- Fan Costumes '09 — "Are you asking for an obscure costume challeeeeeeenge?!"