When I was little I, like, worshipped Halloween. And truthfully, part of me still does. 'Cause it's your one chance all year to be someone else.
~Angela Chase, My So-Called Life
My So-Called Life
Episode 9: "Halloween" (1994)
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Best costume: (tie) Danielle, dressed as her older sister Angela & Rickie, dressed as fellow student Brian Krakow
Will & Grace
Season 1, episode 5: "Boo! Humbug" (1998)
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Will (Eric McCormick) and Grace (Debra Messing) plan to have a night in on Halloween watching movies, but at the last minute Will's client Harlan sticks him with babysitting his kids. For the duration of the episode neither child speaks-- they just sit on the couch with their masks on the entire time.
Best costumes: Harlan's kids as Richard Nixon and a bumble bee
Freaks and Geeks
Episode 3: "Tricks and Treats" (1999)
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High school freshman Sam (John Daley) looks forward to trick-or-treating with friends Bill (Martin Starr), Neil (Samm Levine), and Harris (Stephen Lea Sheppard), and they all put careful time into their costumes. Mrs. Weir (Becky Ann Baker) is excited to hand out treats with daughter Lindsay (Linda Cardellini). But Halloween doesn't meet anyone's expectations-- at the last minute Lindsay ditches her mother to hang out with friends in the "freak" crowd, who are knocking down mailboxes, smashing pumpkins, and egging people; all the trick-or-treaters are throwing out Mrs. Weir's homemade pumpkin cookies; and Sam and his friends have a horrible time trick-or-treating, the worst being when Lindsay eggs her brother Sam.
Best costume: Bill as the Bionic Woman, not only because of his attention to detail in the costume itself, but because of how much he immerses himself into the role of Jamie Sommers. "These aren't bionic, they're all me!" He's also unintentionally creepy.
The Office
Season 2, episode 5: "Halloween" (2005)
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It's the end of the month and Michael (dressed as a two-headed version of himself) must fire someone, but he's not sure who, and stresses about his decision all day long. My favorite scene is when Michael questions Dwight (dressed as a Sith Lord) about who to fire. Michael acts as though he is consulting his second head about possibly firing Dwight. The camera cuts back and forth between two-headed Michael and the black-hooded, intense Dwight who exclaims, "Quiet, you!" trying to silence Michael's mini head.
Best costume: Dwight as a Sith Lord
Mad Men
Season 3, episode 11: "The Gypsy and the Hobo" (2009)
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Don (Jon Hamm) tells Betty (January Jones) the truth about his past and his family. Halloween features into the background instead of being the focus of the show. This episode makes my list because I love the line at the show's very end, directed at Don as he accompanies his kids Sally (a gypsy) and Bobby (a hobo) while they trick-or-treat. After commenting on Sally and Bobby's costume a neighbor looks at Don and asks, "And who are you supposed to be?"
Best costume: Dick Whitman as Don Draper (okay, not really a costume but I couldn't resist)
Parks and Recreation
Season 2, episode 7: "Greg Pikitis" (2009)
Not yet on DVD
Ann (Rashida Jones) throws a very dull Halloween party, and the very person she hoped to avoid, rapper-wannabe Tom Haverford (Aziz Ansari), comes to the rescue by livening things up with music and dancing. Leslie (Amy Poehler) is on the alert to prevent high school student Greg Pikitis from continuing a tradition of vandalizing a statue in the park.
Best costume: Tom as T-Pain
