Halloween might be the time of year to decorate your lawn with pumpkins and ghouls, giving out candy to your neighborhood’s costume connoisseurs, or trying to figure out the most clever costume to wear to the office or to a party. But the best way to celebrate Halloween is through a good old Halloween episode of your favorite TV series. Besides, what would pop culture look like without It’s the Great Pumpkin, Charlie Brown? Or Roseanne’s iconic Halloween episodes?
Bundle up and buckle up as we look back at 10 of the best Halloween TV episodes.
“Halloween” – Modern Family (2010)
“All I ask is that you leave me Halloween. Yeah, Halloween. I realize it is a crazy-ass holiday for a grown woman to care about this much, but it is my crazy-ass holiday. Mine.” And so kicked off the first ever Halloween on Modern Family, way back during season two in 2010. It also introduced us to how passionate Claire Dunphy (Julie Bowen) is about this holiday (by season four, no parents were allowing their children to trick-or-treat at the Dunphys’ house, since the previous year Claire almost caused a man a heart attack with a gruesome prank). She could definitely give Roseanne Conner a run for her money. Elsewhere, Gloria (Sofia Vergara) is made to feel insecure about her Columbian accent for the first time (“maybe she’s never been picked on for bein’ diff-er-ent”), and Claire offers her daughter $10 to go put on more clothes. All in all, a Halloween to remember.
“BOO!” – Roseanne (1989)
Any list of the best Halloween TV episodes would be incomplete without a mention of Roseanne, who certainly invented the Halloween episode as we know it. “BOO!” started it all back in 1989, during the series’ second season, when the Conners set up their house into the “tunnel of terror” to lead their trick-or-treaters through. Meanwhile, Becky (Lecy Goranson) almost doesn’t participate after she is uninvited to a Halloween party (“I hate Marci Michaelson!”) and we are introduced to Dan (John Goodman) and Roseanne’s (Roseanne Barr) twisted game of who is better at scaring the other. But we all know who the master will always be. Don’t miss our look back at the legacy of Roseanne’s Halloween episodes as this year marks 30 years since “BOO!” first aired on October 31, 1989.
“The One With the Halloween Party” – Friends (2001)
“Come on, who are we kidding? I’m Doody.” It took Friends until season eight to have a Halloween episode, which also happens to be one of the series’ strongest and funniest seasons. Sean Penn might be the most notable guest star that comes to mind, but we often forget about a young Emily Osment, who plays a little girl whom Rachel doesn’t have any candy or money left to give to. “Hey, can I write you a cheque?” Her name? Lelani Mayolanofavich.
“Now I Know, Don’t Be Scared” – Desperate Housewives (2007)
The first time Halloween came to Wisteria Lane was the year that Bob and Lee (Tuc Watkins and Kevin Rahm) moved onto the lane and threw a party—right after making an enemy out of the new president of the Homeowners’ Association, Katherine (Dana Delany). Meanwhile, Bree (Marcia Cross) was busy faking a pregnancy to hide her teenage daughter Danielle (Joy Lauren) getting knocked up—but Bree’s ruse is at risk when Danielle suddenly returns home from the convent they had sent her to. But things get even messier when Danielle shows up at the neighborhood Halloween party dressed as Bree…and soon goes into labor. Bree’s son Andrew (Shawn Pyfrom) is also forced to dress up as Cher, and Katherine comes as Marie Antoinette—“you came as a self-important queen who lost all her power! Isn’t that a bit on the nose?”
“Tricks and Treats” – Freaks and Geeks (1999)
Freaks and Geeks might have only had the one Halloween episode, but it’s one of the most memorable in TV history, and it aired 20 years ago tonight on October 30, 1999. Sam (John Francis Daley), Neal (Samm Levine), and Bill (Martin Starr)—the “geeks”—go out trick-or-treating and run into another altercation with their bully, Alan (Chauncey Leopardi). Meanwhile, although Lindsay (Linda Cardellini) had made plans to stay home and pass out candy with her mom (Becky Ann Baker), she decides to go out cruising around town with her new bunch of burnout friends, the “freaks.” But things get a little out of hand when Lindsay unknowingly eggs her brother… a classic example of the show’s groundbreaking attempt at portraying the plight of growing up and finding yourself against the awkward backdrop of high school.
“Orange Alert” – Parenthood (2010)
In this episode of the underrated NBC family drama, the Bravermans celebrate Halloween as Max (Max Burkholder), who has Asperger’s, decides he wants to go out trick-or-treating—despite his fears and aversions to it in the past. As the whole family heads out for a night of costume fun, Max faces his fears and enters a haunted house with his cousins, and Crosby (Dax Shepherd) proposes to Jasmine (Joy Bryant) and everything was good… even if just for a short while. Especially on Halloween, Parenthood did what Parenthood did best: remind us of the comforting warmth and support of your family. Also, can we talk about how cute Adam Braverman is in his baseball player costume?
“Boo! Humbug” – Will & Grace (1998)
Back in 1998, during Will & Grace’s first season, Will (Eric McCormack) and Grace (Debra Messing) thought they were above Halloween. It’s just a holiday for kids. But when their adult night of wine and a movie is interrupted by having to babysit to the kids of Harlan (Gary Grubbs), Will’s boss, they just might find out how to embrace their inner child and figure out that Halloween isn’t just for kids. Meanwhile, Jack (Sean Hayes) convinces Karen (Megan Mullally) to go downtown with him on Halloween in costume, during which an apprehensive Karen is warmly embraced by drag queens—leaving Jack feeling a little left out.
“The Middle-Earth Paradigm” – The Big Bang Theory (2007)
The Big Bang Theory also tried their hand at Halloween during their first season, when Penny (Kaley Cuoco) throws a Halloween party and invites her geeky, awkward new neighbors. They arrive at 7:05, apologizing for being late (the party started at 7:00—they are the first to arrive). Sheldon (Jim Parsons) dresses up as the Doppler Effect, even though nobody gets it, and Leonard (Johnny Galecki) and Penny share their first kiss after her ex-boyfriend crashes her party and creates pandemonium.
“Halloween IV” – Roseanne (1992)
If “BOO!” created the gold standard for Halloween episodes in 1989, “Halloween IV”—from Roseanne’s fifth season—certainly proved they were in fact the Masters of Halloween. In this episode, Roseanne has lost her Halloween spirit after daughter Becky isn’t able to return home for the holiday. The Conners had also had a rough year financially after the foreclosure of Dan’s bike shop, so Rosie just wasn’t feeling it this year and doesn’t attend the Lodge Party. But what’s to happen when the Queen of Halloween doesn’t participate? Roseanne is visited by three ghosts: the Ghosts of Halloween Past, Present, and Future. After remembering how she’s always been good at Halloween, seeing how her friends are making fun of her at the party, and then seeing a future of turning into her mother if she doesn’t go all out on Halloween, Roseanne arrives at the Lodge Party—and gives everyone just the trick they’ve been waiting for. Happy Halloween! *insert Roseanne’s cackle here*
“It’s the Great Pumpkin, Charlie Brown” (1966)
No list of special Halloween episodes would be complete without the one that arguably started it all back in 1966—the first time Linus sat in the pumpkin patch and awaited the arrival of the Great Pumpkin. Everyone said he was crazy and that the Great Pumpkin didn’t exist—which may be true, as Linus is still waiting for him 53 years later—but he never gave up. Every year, he waits for the Great Pumpkin to rise out of that pumpkin patch. And 53 years later, we still tune in to hope this will be the year he finally arrives.