The Roseanne Halloween Episodes Ranked

After hearing late last week that the classic 90’s comedy Roseanne might be making a comeback, I was feeling nostalgic.  Not only was this one of my favorite shows growing up, but I always looked forward to their annual Halloween episodes.  A few years back I picked up Roseanne Tricks & Treats, which features all eight of the classic Halloween episodes.  In honor of the return of Roseanne, I decided to celebrate and re-watch the episodes and rank them based on their Halloween spirit and the pranks.

1. Boo

Roseanne began the tradition of Halloween episodes during its second season.  “Boo,” was the seventh episode of season two and the first Halloween episode to air.  “Boo” ranks number one in my book because it set the tone for the Connors and Halloween for each subsequent year.  In “Boo” we learn just how important Halloween is to the Connors and it sets the precedent for the prank wars between Roseanne and Dan each year to determine who the Halloween Master is.  The vibe of this episode fully embodies the spirit of Halloween in the early 90’s and always leaves me feeling nostalgic.

2. Trick Me Up, Trick Me Down

“Trick Me Up, Trick Me Down” was the third Roseanne Halloween episode and aired in 1991.  This ranks number two in my book for a few reasons, first, it opens with what I feel is the best prank of the series.  After hearing screams, The Connors’ neighbor Kathy Bowman comes over to investigate and discovers Dan gutted and bloody on the kitchen table.  After hearing her scream Roseanne wielding a knife and bloodied quickly swoops in on Kathy leaving her to question if she is next. While she’s distracted Dan sneaks up behind her and she quickly realizes she is part of an elaborate prank.  What makes this my favorite prank is the fact that it’s one of the few pranks where someone is actually terrified and yet the execution is so simple.

Kathy Bownan stands over the body of Dan who she believes has been murdered

The second reason I rank this number two is because this is the first episode where you really notice the show up the production value of the episode a bit.  The costumes are a bit nicer, the sets are more elaborate and it really gives you that fun Halloween vibe.

Finally, this episode introduced the infamous jack-o-lantern end credits where a series of jack-o-lanterns are displayed during the credits with the final featuring a carving of Roseanne.  This was something that was featured in other seasons as well and was a nice way to end the Halloween fun.

3. Halloween IV

The fourth Roseanne Halloween episode ranks third on my list for two reasons.  First, it gives way to the backstory of the why the Connors love Halloween so much. In “Halloween IV” Roseanne loses her Halloween spirit after finding out Becky wouldn’t be returning home for the holiday.  Unmotivated and uninspired on Halloween night, Roseanne stays home to unenthusiastically pass out candy to trick or treaters, but when she falls asleep the show pays homage to A Christmas Carol with the ghost of Halloween past, present, and future coming to visit Roseanne and remind her of why Halloween is so important.

During the past segment, we learn that Roseanne started her pranking at a young age, pretending to choke and terrifying her mother during her first Halloween.  We also get to witness the meeting of Roseanne and Dan during a Halloween dance where Roseanne pranks Dan’s date earning her a spot with him on the dance floor. (Side note, in this specific scene they could not have found better actors to play a young Dan and Roseanne.)

Roseanne with the ghost of Halloween past

In the end, Roseanne comes to her wits after discovering she would become a goody-goody, lose her husband and ultimately turn into her mother.  She ends the episode by dressing up as the Statue of Liberty and heading down to the lodge to celebrate her favorite holiday and to seek revenge on the party goers who she overheard bad-mouthing her during her visit with the ghost of Halloween present.  Roseanne gets the last laugh by lighting lady liberty’s torch and setting off the fire sprinklers drenching the rest of the party-goers while she remained dry under an umbrella.

“Halloween IV” also features my second favorite prank from the series where Dan pretends to get his hand caught in the garbage disposal spewing blood all over the kitchen, terrifying Jackie.

4. Halloween V

Roseanne’s fifth Halloween installment is fourth on my list not because of a particularly strong storyline, but because of the caliber of pranks in the episode.  As always Dan and Rosie are trying to one up each other with pranks on Halloween and in “Halloween V,” Dan pulls my third favorite prank of the series.  While working at the Lunch Box, Roseanne teases a customer at the counter, after having enough of her Halloween jokes, he loses his cool and pulls a gun robbing the store.  Roseanne thinks the whole thing is part of an elaborate prank and plays along by emptying the register, giving him her house keys along with her address, and ultimately her wedding ring.  As the drama unfolds Jackie tries to reason with Roseanne, but Roseanne can’t be swayed after all this was just a prank. Or was it?  After Jackie reveals Dan’s “real” prank Roseanne is terrified realizing she just gave an armed robber her wedding ring.  As she runs out the door to see if she could see where the man fled, Dan enters the scene and confirms Roseanne’s original suspicion that it was all a prank, but not before everyone had already convinced Roseanne otherwise.

Another great prank from this episode is the prank that wasn’t.  A big part of “Halloween V” is about how much Dan dislikes Nancy, the co-owner of the Lunch Box.  Throughout the episode Roseanne tries to get Dan to tell Nancy he likes her and even consider pranking her in order to keep peace at the diner.  In one of the final scenes of the episode Nancy walks in on Dan and Roseanne talking about it, unannounced to them.  After realizing Nancy overheard him, Dan runs after Nancy but gets hit in the face with the kitchen door as it swings back, breaking his nose.    After seeing his face and nose covered in blood Nancy thinks she’s finally being pranked by Dan, not realizing the damage is real she squeezes his nose causing him to howl in pain.  Roseanne plays along realizing Dan is really hurt and convinces Nancy to go look at her look of surprise in the mirror while she rushes Dan to the ER.

“Halloween V” closes with another elaborate prank that builds throughout the episode.  In his first appearance in a Halloween episode, David shows interest in a new girl named Sally while Darlene is off at school.  As Roseanne watches things develop she is also in contact with Darlene who has confessed her love for David and explained how she has opted to not see a guy at school because of it.  At the end of the episode, Roseanne and Dan come home to discover that Sally is in the basement with David.  When Darlene returns home unannounced they try to prevent her from discovering the two, but DJ blows their cover and tells Darlene he saw the two kissing on the couch and now they’re in the basement.  After telling them to stay put, Darlene runs to the basement, which is followed by Sally’s screams.  When the Connors enter Darlene is on top of Sally and with the aid of a dummy head, beheads her.  The prank gets Roseanne, but in the end, David reveals he did it to try and impress her and show he was part of the family, which earns him little more than a hug and a snide remark.

5. Trick or Treat

“Trick or Treat” was the second Roseanne Halloween episode and features Darlene’s infamous stomach monster scene, but while the costumes improved in the second Halloween installment (Dan’s Three Stooges and Becky’s mutilated prom queen are also great), the storyline itself fell flat.  Most of the episode is spent in a bar where Roseanne is dressed up like a man and discovering all the nuances that come with being one.  Overall the episode lacks the fun Halloween spirit that the initial installment created.  Most of the cast is bummed out about something and the majority of the episode is spent exploring these more serious issues like a dad being upset that his son dressed up like a witch and whether or not it’s ok for a guy in a bar to grab a woman to force her to dance.

Darlene's stomach monster waving

6. Skeletons in the Closet

While this episode isn’t necessarily bad, there really isn’t anything that memorable about it.  The entire episode is built upon the idea that gay characters Leon and Nancy are going to take the title of masters of Halloween from “the breeders.”  While Roseanne was considered a gay-friendly and progressive show for the time, it was interesting to see just how much “Skeletons in the Closet” used gay stereotypes to build the storyline.  The main prank in the episode was convincing Roseanne that Jackie’s husband Fred was previously gay and is now pretending to be straight, hence the “Skeletons in the Closet” title.

7. Halloween: The Final Chapter

This made number seven on the list, one because it exists, and two because it isn’t “Satan Darling,” the final Halloween installment that aired once Roseanne had completely jumped the shark.  This bizarre, acid trip of an episode might actually be better high, but I haven’t tried it yet.  Featuring a Quija board, the spirit of Jerry Garcia and some off the wall cameo’s this is an episode most Roseanne Halloween fans can probably skip.

8. Satan, Darling

The real final chapter in Roseanne’s Halloween adventures is like the rest of the show after the Connors won the lottery; garbage.  Though it guest stars Absolutely Fabulous characters Edina and Patsy, there is nothing fabulous about this episode.  After passing out drunk in a bathroom Roseanne has a dream that spoofs Rosemary’s Baby in which Darlene gives birth to Satan.  This entry in the Roseanne Halloween mythos is as forgettable as the last two seasons of the show and I regret it every time I rewatch it.

Where do you rank the eight Roseanne Halloween episodes? Let me know in the comments!

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