Pupcast and Best Halloween Television Episodes

“Halloween”

It is hard to pick which Halloween episode of The Office is my favorite, because they are all great. The actual episodes have incredible writing, that really mimic life in an office on the holiday, but the thing that makes these specials really stand out are the costumes. The best ones are a toss up between Jim's random “non-costumes” and the very meta-characters who dress up as other characters from pop culture. Jim is usually the unwilling participant, that realizes how silly it is to dress up for Halloween at work, and his costumes reflect that perfectly; 3-Hole Punch Jim, Dave and BookFace are all amazing. There are too many to list of the pop culture costumes category, but my favorites are the 3 dueling The Dark Knight Jokers in "Koi Pond", Kelly as Carrie from Sex and the City, Ryan as Justin Bieber, but I cannot forget Michael Scott as Dick in a Box, about a year too late. However, while the costumes are always great, my favorite episode is Season 2's "Halloween" in which Michael Scott dresses up as "attached to a paper mache likeness of your own head". Yes, you read that right. In this episode Michael is tasked with firing one of the Dunder Miffilin Scranton employees and to see this all play out while they workers are dressed up (Hello, Dwight the Sith Lord) is incredible.

"Tricks and Treats"

My Marathon to Start on Freaks and Geeks is coming soon and I was inspired to write it after recently going back to watch the Halloween episode. The show overall deals with adolescence in such a perfect way, but this episode especially captures many of the issues and struggles teenagers (and parents) deal with on the holiday. The episode begins with Sam and his friends trying to decide if they should go trick or treating or not. They are freshman in high school and must decide at what point they are too old to be part of the “kids” tradition. I know we all had to make this decision, and it was not an easy one! This year, the boys decide to hold out and put on their best (or worst costumes), but after the disaster their experience becomes, I think they probably wish they had stayed home. Also, Bill's costume of the Bionic Woman is worth your time simply to see possibly the most awkward costume of all time. On the freaks side, Lindsay also has to make some big decision as she decides if she will stay home and hand out candy with her overly excited mother, or go drive around and get into trouble with her new friends. Since she is becoming a rebellious high school teenager, of course she chooses smashing pumpkins and mailboxes with her friends, but by the end of the night, she also wishes she made the other choice. I also think one of the most heart-breaking stories is watching Mrs. Weir prepare for her favorite night with her daughter, and how her spirit diminishes after everything goes wrong (after Lindsay ditches her) and all of her joy of Halloween has been ripped away. Overall, it truly shows many aspects of the holiday and the ups and downs we all have been through surrounding adolescence and parenting. The writing and realism makes it one of my favorite episodes…ever.

Any or all episodes

We go a bit in to depth on The Treehouse of Horror in the podcast, but no way they could be left off the list, as have become the quintessential yearly Halloween special. The Treehouse of Horror episodes began during the second season of The Simpsons and have been a staple of the series ever since. Each episode is split up into three different sections that all somehow put the family and residents of Springfield in a creepy, horrifying or science fiction type setting. The episodes also stand-alone in that they are coherent themselves and do not fit in with the current storylines of the series and are completely separate. It’s hard to believe The Simpsons is in its 24th season, and because that, the Treehouse of Horror has been a part of Halloween as long as I can remember and should be recognized as one of the best holiday traditions.

"Pinkeye"

Speaking of Raggedy Ann, ladies around the world, have had trouble getting their significant others to dress up in couples costumes ever since South Park’s Halloween episode “Pinkeye”. Stan shows up at school dressed as Raggedy Andy, but is horrified and embarrassed when his girlfriend, Wendy, bailed on being his Raggedy Ann counter-part. The fear of being the lone part of a lame costume might be the most horrifying prospect of them all. The episode is also brilliant with its play on zombie culture after Kenny is turned in to a zombie when the mortician’s embalming fluid is mixed with Worcestershire sauce. It’s so weird, but it’s so South Park. Oh, and don’t miss the moment Zombie Chef and his gang zombies perform their Michael Jackson “Thriller” rendition of “I’m Gonna Make Love Even When I’m Dead”.

“Boo”

I never really thought I would ever put Roseanne on one of my best lists, (even though I have likely seen every episode of the show) but it deserves it in this category. Roseanne knew how to do Halloween. Every year the Connors put on a great show, because Halloween was their favorite holiday and they went all out. They are all worth watching, but if I had a choice it would be the first in which Roseanne plays jokes on Dan while he is waiting to hear about a business deal. But…is the joke really on her?! The resolution of this episode has always been etched in my brain since childhood. An honorable mention has to go to “Halloween IV” in which Roseanne has a Christmas Carol like experience and learns that she must never ever (ever) lose her Halloween spirit.

"Epidemology"

Zombies are a staple of Halloween. The Walking Dead wasn’t technically a Halloween episode, the fact the series premiered on the night of the holiday, made it a pretty epic Hallow’s event. However, if you want another true Halloween episode dealing with zombies (that isn't animated a la South Park), look no farther than Community. The gang gets trapped in a zombie movie after the dean orders a bunch of old army rations from a military surplus store. The episode follows the standards of a horror movie, and it is amazing. But, wait, that’s not all…there is a Troy and Abed Aliens-inspired duel costume. Could you want anything more from a holiday episode?

I’m not sure there is a more classic episode of Halloween television than It's The Great Pumpkin, Charlie Brown. It is hard to believe that the special that first aired in 1966 and it is still relevant and popular today. It is still part of my yearly Halloween tradition and I am probably much too old to admit that. I can’t imagine anyone having not seen it yet, but if you have not – watch it, watch it now. The plot revolves around the Peanuts gang's Halloween adventures. Linus, misses out on most of the activities because he is stuck in the pumpkin patch, waiting for the Great Pumpking since he believes he is finally going to show up this year. While he is stuck there Charlie Brown is off getting rocks instead of candy. Sad. It’s an episode that only the Peanuts could do, and is a truly special Halloween special.

"Halloween Costume Ideas"

It feels odd to say because he is so unfunny now, but Adam Sandler’s Halloween Saturday Night Live skit is still one of my favorite sketches of the show. He gives suggestions to kids as to what cheap Halloween costumes they should wear simply using their face. Crazy Pick Mustache, anyone? Now give me some candy. If you haven’t seen it yet, just watch it here.