The movie follows eleven-year-old Kenny (Dan McCann), his best friend Doug (A. Michael Baldwin), and tag-along Sherwin (Jeff Roth), a younger boy who lives across the street, during the days leading up to Halloween.
Kenny & Company contains examples of:
- Animated Credits Opening: A jack-o-lantern that opens and closes its mouth to reveal different names.
- Ashes to Crashes: The Bully Johnny Hoffman (Willy Masterson) has Kenny cornered. He throws books at Johnny, which only slow him down. Then he grabs the nearest thing available - the urn of the house owner's husband's ashes - and throws them in Johnny's face, which blinds him long enough for Kenny to get in a good punch.
- Bystander Syndrome:
- Kenny and Doug leave a dummy lying in the road to prank drivers. A car screeches to a halt in front of the dummy, and a male voice says, "Holy Christ, Martha, it's a dummy!" A female voice says, "George, don't run over his head!" The car then maneuvers around the dummy and goes on its way, with neither person making any effort to get help.
- Later, Kenny and Sherman witness a car crash in which a man is badly injured and possibly killed. Instead of calling for help or waiting for the police, they flee in terror.
- Character Narrator: Kenny's voice-over provides background information, as well as his inner monologue.
- Cut His Heart Out with a Spoon: Kenny and Sherman are describing what they'd like to do to Johnny.Sherman: I'd like to stick his head in the toilet and flush it down until he was drownded!
Kenny: And I'd like to cut off all his fingers and jam them up his nose.
- Death Is a Sad Thing: After Kenny's beloved dog Bob is put down, he asks both his dad (James dePriest) and the elderly Mr. Brink (Clay Foster) what happens after you die. Dad admits that he doesn't know, while Mr. Brink tells him that there's no afterlife, paradise is on Earth, and if you have kids you can live on through them. Kenny doesn't seem entirely satisfied by either one.
- Drink-Based Characterization: Kenny tries to invoke the "tough guy" version by ordering a Suicide, which is all six flavors of slush mixed together. It tastes like mud, but it makes him look cool in front of his teammates.
- Frame-Up: Kenny lures Johnny into a mean old lady's house. Then Doug ties the door shut while Sherman calls the police to say that Johnny has tied the door shut and is now trying to shoot the owner of the house.
- Groin Attack: Once Kenny has Johnny incapacitated, he kicks him in the crotch.
- The Klutz: Kenny and Doug try to keep Sherman out of their workshop because he breaks everything he touches.
- Own Goal: Narrowly averted in the opening scene. Kenny runs in the wrong direction with the football, but Doug runs after him, pulls on his shirt, and says, "Other way, dummy."
- Only Known by Their Nickname: Pudwell (David Newton) has been going by that name for so long that Kenny doesn't remember his real name. Even his mom calls him Pudwell.
- Prank Call: Kenny, Doug, and Sherman kill time on Halloween afternoon by calling random people, saying they're going to be working on the phone line for the next five minutes and if the person answers the phone during that time, they'll receive a horrible electric shock. The kids then call the person again, and when the person picks up, they play a recording of Sherman screaming while the garbage disposal chews up an apple.
- Protection Racket: Johnny demands protection money from Kenny, and beats him up if he doesn't have anything.Kenny: Me and Sherman and a couple other kids have to pay him protection money.
Dad: Well, what's he protecting you from?
Kenny: I don't know.
- Razor Apples: Mr. Donovan (Reggie Bannister) warns the kids to be careful with candy apples and popcorn balls, which have been known to contain razor blades and rat poison. On Halloween night, a creepy-looking guy gives Kenny, Doug, and Sherman each a popcorn ball; once the guy's door is closed, they throw the popcorn balls back at it.
- The Stinger: There's one just a few seconds long, of Big Doug handcuffing Johnny and saying, "And that's the way handcuffs work."
- Super Window Jump: Johnny escapes from the old lady shooting at him by diving through her window.
- Wedgie: Johnny gives Sherman such an aggressive wedgie that his underwear rips out of his pants.
- William Telling: Doug's dad Big Doug (Ralph Richmond), a secret service agent, has Doug balance wine glasses on the backs of Kenny's hands, then draws his gun and says he's going to shoot the glasses. He doesn't actually fire, but Kenny is so terrified he jerks his hands down, smashing the glasses on the floor. The Dougs find it hilarious, Kenny less so.