Who Can Stay Homeless the Longest?
1 - Must sleep outside.

2 - No outside help can be made by the crew, family or friends.

3 - No wallets, cards, phones.
Spenny receives a knee to the testicles, courtesy of Kenny.
Original airdate
January 7, 2007

Who Can Stay Homeless the Longest? is the twelfth episode of the third season. Kenny and Spenny must sleep outdoors for three days, at the start of which they are stripped of all belongings besides the clothes on their backs. If either competitor sleeps within a domicile or any type of establishment before the three days expires, the other man wins.

The CompetitionEdit

Kenny begins with his usual slander of Spenny, and Spenny fears Kenny will enjoy the competition as he will be stripped of all responsibility. Spenny assigns himself a secondary goal, apart from winning the competition, in that he wants to genuinely experience the life of a homeless person. 

The guys go to a nearby park to begin the competition. Each claims a bench for himself until Spenny decides to ponder the average homeless person's schedule, and Kenny uses the opportunity to throw dirt in his face to start a fight, which ends when Kenny steals Spenny's shoe and throws it in a bush. Spenny demands one of Kenny's shoes while searching for his own, which he eventually finds. Kenny offhandedly says he could get Spenny arrested for assault.

Spenny sets off to begin his new temporary life by stealing a shopping cart. Both men scavenge for any useful materials and leftover food in waste bins and alleyways. Kenny finds a plastic fast food cup on the ground, and tricks the cashier into giving him a new one, as he claims it was spilled by an imaginary son of his. Kenny enjoys life as a homeless person, while Spenny washes his hair in a decorative fountain and is kicked out of the plaza by a security guard. He quickly loses energy and begins to lounge around near the end of the day. Kenny and Spenny meet up in an underpass where they spend their first night. 

The next day brings rain, and Spenny uses cheap jokes to con money out of passersby. Kenny amuses himself in a bus stop and is locked out of the production van by the crew. Spenny quickly becomes angered at the entire situation and berates Kenny, whom Spenny imagines is enoying himself throughly. Kenny is sitting on a sheltered staircase, which leads into his bank. He has a sudden epiphany and enters the bank, and withdraws money without the use of his card. He makes a point to the camera by going to one of the most expensive restaurants in Toronto and sampling many dishes. 

Spenny has more or less adapted to his new lifestyle, panhandling for money and attempting to haggle shop owners for food. He hopes Kenny will forfeit the competition, but isn't so gullible as to believe that Kenny hasn't been using loopholes in the rules to make life easier for himself. They once again meet up at the underpass for their second night of homelessness. 

Then next morning, Kenny visits the house, lamenting the fact that he "used to" live there. Spenny begins to feel ignored while panhandling, and the cup he is using to collect change is knocked out of his hands by a passerby. Meanwhile, Kenny amuses himself by making parody cardboard signs which read messages such as "Vagina Shave $5" and "Spenny Molested Me". 

Spenny makes eleven dollars panhandling, and uses the profits to buy himself sun block. In a park, Kenny considers visiting the bank for more money, and is visited by a passing Spenny. A police car makes rounds around the park, and sees the guys with film crews. The police tell them they can't film in a public park, and Kenny claims that they are filming a documentary about crack addicts, and snidely calls Spenny the aforementioned, which earns him a punch in the arm. The police take action and haul a distraught Spenny away into their car and drive off, leaving Kenny and the crew unsure of what to do. 

Later, Spenny admits that he spent the third night of the competition in a holding cell, and thus lost the competition.