Actually on time-ish now. Same rules, listed from worst to best.
9: Jeffy's Halloween (4/10)
At the very bottom is this video, and what can I really say? It's just plain mediocre in every way. A few decent jokes here and there but mostly just a dull experience I forgot about quickly afterwards.
8: Shrek's Costume (5/10)
Okay I gotta be honest. Black Yoshi carried this video on his back like Hercules. This video has a case of "bad first half, good second half". The first half was kinda bad if I'm being real, but Black Yoshi's actions in the second half and the post credits scene definitely added some needed laughs to the second half with his reckless attitude.
7: Bowser Junior's Halloween (7/10)
Just an average good 2014 era video for me. Nothing that stands out compared to other videos from the period but it has that same laid-back and chill attitude I love from the 2014-16 period, where it's basically just Junior and co. traveling to houses, talking and collecting candy (and other assorted objects) and that's it.
6: Happy Halloween (7.5/10)
Now we're getting to the really good stuff. The video's biggest strengths are it's two amusing dual plotlines with a solidly engaging killer clown plotline in the first half and a simpler but just as funny B plot of Mario and Jeffy trying to get a weird person's candy. I feel the back and forth switches were perfectly timed and the payoff for the killer clown plot was great. As for the big con? So much screaming. It makes sense given killer clowns and all that but it really makes it hard to watch sometimes.
5: Bowser Junior's Halloween Problem (7.5/10)
Similar to "Bowser Junior's Halloween" it's mostly just Junior and co talking and walking around, but this time there's a few funnier standout moments, the best of which has to be Chef Pee Pee's chainsaw murder scare prank. This could easily be swapped with the video above depending on how I feel though.
4: Bowser Junior's Halloween Heist (7.5/10)
One of the most creative and unique of the Halloween specials. The whole premise has an air of complete stupidity surrounding it but I feel like it works excellently this time since the plot itself is also rather complex and has a good variety of characters involved, and I feel all of them work well in the video.
3: The Zombie Apocalypse (7.5/10)
Not the zombie apocalypse video I quite expected from SML, but I'm fine with this result too. I do like that there's more comedy in here than a normal zombie-themed special would be. While there is a feeling of intensity throughout the video, almost all of the action is immediately followed by a funny but awkwardly placed one liner, which I actually quite like. So not what I was hoping for but still a good final product.
2: Joseph's Mom (8/10)
Unusual for an SML video, it's not much of a comedy. It's more of a dramatic video. I'll keep it breif since I think almost everyone knows how this video ends but basically it's revealed Joseph's mom ditched Joseph to live on her own and the whole topic is handled with so much tact that it hits hard. The ending is still one of my favorite in any SML video. The bittersweet nature is really something else and unmatched by most other SML videos.
1: The Costume Contest (8.5/10)
Funnily enough, considering 2018 is my least favorite legitimate SML Movie year, it has my favorite Halloween special. It's widely considered a classic and I definitely see why. This video is a nonstop barrage of hard hitting jokes and almost all of them hit, and not only is it some of the funniest material the show's pulled off in years, but it couples that with a solid plot and character roster where no one feels out of place. My only con is that some of the jokes feel a bit awkwardly paced (which is why the score isn't 9), but this doesn't stop the video from shooting to the top of my list. This might even be one of my favorite SML videos ever and probably one of the best executions of the rapid fire comedy template.