Kenny vs Spenny Wiki
Who makes the most convincing woman?
Rules
None.
Winner
Spenny
Humiliation
Kenny, dressed as Kendra, walks the street of an area known for prostitution
Original airdate
January 28, 2004

Who makes the most convincing woman? is the 18th episode of the first season. Kenny and Spenny must portray themselves as women in a cocktail party with five female judge that decide the winner based on the two's behavior and antics.


The Competition[]

Kenny states his dislike while exaggerating Spenny's advantage in this competition Kenny comments on Spenny being almost a woman already and wears lingerine and Spenny flashes his boxer brief in response. Spenny then concludes that this competition will be good for the two's feminine side.

Whilst peeing while sittin down, Kenny emphasize the importance of voice, looks and disrupting Spenny's character during the cocktail party. He then stuff his shirt to imitate boobs while brainstorming female names akin to his own. (Kenita, Kenriata, Kennisa, Candy, Kensuela, Kiki, Kendra)

Spenny meets with Catherine Bell, an image consultant, and suggests his idea of a non-overly feminine, working woman who has a family. He then further solidifies his idea by saying that the woman is an editor and married to 42 year old Bill and has a 6 years old Kevin and 4 years old Cathy. Catherine is impressed by the idea and suggest they work on some other thing with Spenny brining up his concerns for the voice. Kenny visits the shopping district and interviews various girls for advices on being a woman; The advices being more touchy-feely, having a closer shave, walking in heels, getting waxed, having conversations about clothes, boys, other girlfriends, sex. Kenny then inquires about breast and hip sizes, asking if he could feel the interviewees' for the sake of reference; He ends the interviews by trying to steal a kiss with all the girls.

Spenny makes progress on his woman voice practicing to Catherine. Meanwhile, Kenny makes a phonecall to Jules, Spenny's uncle, inviting him to the cocktail party.

Kenny visits a 'store that specialize in turning men in to women' and tries out corsset, pantiehose and bras while re-iterating how happy he is to be a guy. Impressed on how real the fake breast feels, Kenny invites the crew to squeeze it, only to slap their hands when they do. During the make-up process, Kenny wonders if he would go all the way on a first date with himself and then kisses himself in the mirror.

Later, Spenny is still ranting about racism, and his plan is to show the judges that he understands their plight as black people in order to beat Kenny. In his room, Kenny is putting on a costume and dressing up, complete with blackface (though not in the exaggerated way it is usually protrayed). He interrupts Spenny's rant, shocking Spenny with his racist tribal costume and bone club, stating that this new character is how Spenny sees black people. After Spenny defends himself from Kenny's lies, Kenny has another costume change, this time transforming into Clarisse, Spenny's old maid. He prepares food in the kitchen, where he is seen by Spenny and mocked for his portrayal of Clarisse. Tired of Kenny's gags, Spenny plays along, and orders Kenny to prepare some food and clean the house, all the while enduring Spenny's disparaging comments. 

The judges, Cyrus, Steven and JR, eventually arrive. Spenny is the first contestant to show them a good time, and introduces himself. He tells them that he has a surprise in store for them, and brings them out to the production van. He gets mad at his crew when they ask the judges to seat themselves in the back, and Spenny berates them for recreating the Rosa Parks incident. While Spenny brings the judges to their destination, Kenny imagines the boredom the judges are sure to experience, and informs the camera that he has invited a black cleaning lady over for an interview and a cleaning session; he wants to "study" whether or not having a black maid means Spenny is racist. The cleaning lady arrives and she is questioned by Kenny, who is very courteous. Soon after she begins cleaning. 

Spenny has arrived at a cottage, a banner on which is emblazoned "Spenny's Race Relations Retreat". He provides the judges with matching outfits bearing the name of the "resort" and sits them in a circle, and Spenny recounts his struggles with his own personal racism. Cyrus and JR have trouble taking him seriously. Back home, Katy, the cleaning lady, is washing the dishes while being observed by Kenny. He fesses up to her about dressing up as Clarisse to get a rise out of Spenny. She then sets herself to the task of making Kenny something to eat, and Kenny strategically places himself where Spenny was standing during the Clarisse gag. 

Spenny is still asking himself rhetorical questions in front of the judges, questioning whether or not he is subconsciously racist. The judges weigh in on his situation, and Steven gives Spenny some very philosophical advice. Steven in particular is very invested in Spenny's case and offers his support. Back home, Katy is still fixing up the house, and urges Kenny to apologize for his previous behavior towards Spenny. 

Spenny eventually moves his party outside, where Spenny has scheduled activites like playing with flying discs, canoeing and playing musical instruments, all the while further questioning the judges. At the house, Kenny's conversation with Katy has gotten a lot more casual, and he begins joking around somewhat. Meanwhile, Spenny's conversations with the judges, having moved past the initial awkward phase, has moved on to determining the truth behind stereotypes. As the day wears on into its end, Spenny thanks the judges for understanding his situation. The scene cuts to a man dressed in Ku Klux Klan walking along the side of the house, ready to meet with Cyrus, Steven and JR.