Whether you are the kind of person who tries to avoid the office costume party, or are the type of person who hates being scared by nerve wracking horror films, watching the five funniest Halloween episodes in TV is a sure way to elicit enough nervous laughter to keep you distracted during the creepiest of holidays. Halloween is the kind of holiday in which television sitcoms can take advantage of the chance to dress characters up in wild or scary costumes and put them in outrageous situations that they may not normally find themselves in.
“Roseanne" "Boo!” (1989) The first of many Halloween specials introduces us to the Conner family’s love of the spooky holiday. The entire episode follows Roseanne and company as they prepare the house and their costumes for the evening’s trick-or-treaters. As the day progresses, Roseanne and Dan hilariously try to out prank each other while Becky decides she is too old to go trick-or-treating. The quick-witted, scathing humor that made the show so cutting-edge in the late 80s succeeds in bringing out the funny side of the scariest night of the year.
“The Simpsons" "Treehouse of Horror” (1990) When Marge steps out from behind a red curtain to issue a warning to parents to put their children to bed because the Halloween episode of “The Simpsons” will be “really scary,” you know you are in for a treat. In the first installment of the “Treehouse of Horror” series, Homer listens in on the kids telling scary stories in the tree house. What follows are three installments of “Twilight Zone”-style tales of terror. “Bad Dream House” is Bart’s tale of an evil house that turns the family into blood-thirsty murderers. His follow up, “Hungry are the Damned” is the story of the family being abducted by aliens that plan on “having them” for dinner. The final installment is a reading of Edgar Allan Poe’s “The Raven,” as performed by Homer, with Bart as the antagonizing bird.
“South Park" "Korn’s Groovy Pirate Ghost Mystery” (1999) When heavy metal band Korn plans a stop in South Park for a Halloween concert, it is just in time to help Stan, Kyle, Kenny and Cartman exact revenge on a group of fifth grader bullies. In the process, the band sets out to solve the mystery of the pirate ghosts that have begun threatenin the town, because, according to lead singer Jonathan Davis, “If there’s one thing we love doing more than playing music, it is solving a groovy mystery!” This comical “South Park” Halloween special is produced in the style of and pays homage to the classic spooky cartoon of the 1970s, “Scooby-Doo.”
“Community" "Introduction to Statistics” (2009) One of NBC’s funniest comedies, “Community” was just gaining momentum when the show’s seventh episode coincided with the Halloween weekend. In “Introduction to Statistics,” Annie throws a Dia de los Muertos costume party for extra credit and invites the study group to attend. Jeff tries to distance himself from the group as he pursues his Statistics professor, but can’t help but to come to their aid when Pierce, wearing a hysterical “Beastman” outfit, freaks out after taking some pills he received from Starburns. Abed as Batman and Troy as “Raw”-era Eddie Murphy only ups the hilarity level.
“The Office" "Costume Contest” (2010) With the 2011 Scranton/Wilkes-Barre Coupon Book (worth over $15,000 in savings) as the grand prize, the employees of Dunder Mifflin go all out for the Halloween costume contest that Pam has organized. Michael Scott is in rare form under the guise on MacGruber, the “Saturday Night Live” parody of “MacGyver.” But when Darryl by-passes Michael and takes some of his ideas to corporate, Michael decides to change his costume and dress as Darryl, hoping to call him out on the perceived deception. Meanwhile, Pam and Jim obsess over Pam’s past relationship with a new employee. “The Office” adds its brand of uncomfortable and sometimes painful comedy to one of America’s creepiest holidays.