Who Can Stay Handcuffed the Longest?


Winner    Kenny
Cheating?    No

Season One Episodes:

  1. Who is the best Fashion Designer?
  2. Who can stay awake the longest?
  3. Who is the better chef?
  4. Who can stand up the longest?
  5. Who can sit on a cow the longest?
  6. Who is the sanest?
  7. Who can earn the most money in three days?
  8. Who does she like better?
  9. Who can stay blindfolded the longest?
  10. Who can win a beauty pageant?
  11. Who can win a series of mini-competitions?
  12. Who can lose the most weight?
  13. Who can stay handcuffed the longest?
  14. Who can put on the best concert?
  15. Who is the best parent?
  16. Who do kids like most?
  17. Who is the strongest?
  18. Who makes the most convincing woman?
  19. Who is the best actor?
  20. Who is the best male stripper?
  21. Who is the best figure skater?
  22. Who can survive in the woods the longest?
  23. Who will use their arms first?
  24. Who can win a court case?
  25. Who can live in a van the longest?
  26. Who is the better boxer?

All episodes: 12345

""Wolfish, shut the fuck up!"" — KennyWho can stay handcuffed the longest is the 13th episode in season one of Kenny vs. Spenny. Due to the vague title, it could be confused that they were handcuffed separately, when in fact one hand from each competitor is handcuffed to the other.


When Kenny and Spenny started, they originally were going to hit and annoy each other in an attempt to make the other submit, but eventually, they made a truce to not annoy each other, and they both agreed to only use mental warfare. After a while, Kenny brings Spenny to the airport to pick up David Wolfish, a man who Spenny owes $10000. Wolfish does annoy, however he also annoys Kenny, who is actually more annoyed then Spenny. Realizing his plan has failed, Kenny kicks Wolfish out of the house. Spenny then asks Kenny if he will come to a draw with him, and, winking at the camera, Kenny agrees. When Spenny unlocks himself, Kenny tells Spenny that he winked at the camera, meaning that he was not truthful of agreeing to a draw, and that he has won the challenge. Spenny is annoyed by this technicality, but he eventually accepts this.


Spenny is to put a fake herpes sore on his face, and attempt to pick up girls for a cup of coffee.



  • An onion rubbed on his body and eaten, fish sauce, and fermented shrimp paste, to irk Spenny because of the smells.
  • Throws a birthday party for Spenny, one of his phobias.
  • Bringing David Wolfish, a man who Spenny owes $10000, to annoy him. However, this method backfires when Kenny is also annoyed.


  • Earplugs, to resist Kenny's annoying noises.
  • Vapour lotion on his nose, to stop Kenny's smells
  • A Kazoo.
  • At points he relies mostly on willpower.


There is no cheating, though the winking part could be thought of as cheating.


  • According to Spenny, he owes Wolfish money as a result of a failed film, which Spenny promised would make enough money to pay back.
  • Due to the fact that they were right beside each other, to do the confessionaries, the one who was not talking had to put on headphones with blaring music.