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Original Air Date: April 27, 2008
Brooklyn, 1986
CHRIS has had it — he’s tired of being a nerd, so he decides he’s going to be cool from now on. The only problem is he has no clear idea what constitutes cool. Worse, no matter how hard he tries to look cool, he just looks more ridiculous than normal.
Chris decides to ask the coolest guy he knows, JEROME, for advice about the subject, and he suggests Chris take pointers from the coolest guy on the planet, rapper LL Cool J. After telling Chris he should adjust his attitude, head gear, and walk and start hanging with cool people to be cool by association, Jerome also pops Chris’ collar and rolls up one of his pant legs like LL Cool J does.
At school one day, Chris learns from GREG that the cool guys who have the nice cars and hot girls are all suspended and failed students who hang out at the arcade. One drives up and asks Chris for a cigarette, leading Chris to think what he needs is to add a cigarette behind the ear to his new image.
Chris gets the cigarettes from his afterschool job at Mr. Harris’ store — he buys them when the grocer goes to the bathroom — and then convinces a terrified Greg to play along. Unfortunately, Greg immediately confesses he got the cigarette from Chris when MS. MORELLO catches him. The result? Chris is suspended from school.
More misfortune heads Chris’ way when he learns TONYA intercepted the call to his parents from the principal, and she bribes Chris into paying her $15 — $5 for each day of his suspension — to keep quiet.
The first day of his punishment, Chris goes to school as normal because he doesn’t know where else to go, and he bumps into the cool group while standing outside with a cigarette still behind his ear. They’ve nicknamed him Juicy Fruit and allow him to hang out with them at the arcade when they learn he’s been kicked out of school just like them.
The cool factor looses its glow when, on the second day, JOHNNY BOY and TRIXIE decide to let Chris tag along when they go pick up VITO, who’s just been released from jail. Vito immediately decides that Chris will tag along with them again in a few days, where he’ll serve as a lookout while they commit a crime. Although the cool crowd doesn’t know it, the cops have been following them for a while.
Not wanting to give up his cool status, Chris is torn. So he discusses his predicament with Mr. Harris, who explains that a lookout is an accessory who can be charged with the same crime as the actual perpetrators. More afraid to go to jail than to be on the bad side of the cool crowd, Chris runs when a patrol car drives by instead of blowing the whistle Vito instructed him to. Greg, who wanders by while Chris is looking out, isn’t far behind.
Elsewhere, ROCHELLE becomes furious when she finds a coat in the closet while spring cleaning that JULIUS‘ old girlfriend Janet gave him. Ever thrifty and cheap, Julius refuses to comply with Rochelle’s demand that he throw the coat out because it’s in perfectly good condition.
Rochelle gets back at her husband by starting to dress in outrageous outfits, simply because they’re in perfectly good condition, too, no matter how awful-looking. Julius finally caves in when she walks up to him when he’s at the barbershop, dressed in clothing with a tacky assortment of patterns and bright colors.
In an ineffective subplot — because it wasn’t funny and didn’t really seem necessary — DREW becomes obsessed with a so-called Rufus Cube that’s just like a Rubik’s cube. He gets it from a homeless man, and ultimately gives up trying to solve it. When he throws it away in a sidewalk garbage can, a pretty girl walks up and confesses she hates Rufus Cubes, too. Drew ends up with her telephone number after she invites him to play Monopoly some time, driving home Chris’ belief that Drew succeeds even when he fails.
Although Chris thinks he’s cool now since he didn’t deliver as a lookout, the final scene takes place in a police room, where a group of detectives discuss tracking down Chris — Mr. Cool aka Juicy Fruit — who they believe is the leader of the cool crowd of punk criminals (it would be the black one, of course, even though he’s obviously only a kid).
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