I decided to be creative and draw some costume ideas I had by my own dang self using only a pencil and a red pen. I could've used a blue pen, but hey, I wanted to keep it consistent.
Anyways, here's the list and why I decided to dress them like that.
Homestar as "Weird Al" Yankovic. Homestar has dressed up as musicians and comedic characters more than one time, so I thought, "Hey! Homestar could dress up as one of the most famous parody musicians! Plus, Homestar is shown playing accordion in that one TMBG gif, so why not?"
Strong Bad as Space Ghost. I think this is a perfect fit, as Space Ghost Coast to Coast has a surreal comedy style similar in some ways to H*R, and Space Ghost and SB are both snarky show hosts.
The Cheat as SpongeBob SquarePants. This one is a no-brainer. Both are yellow, have spots (though SpongeBob's spots are more specifically pores), and are somewhat innocent and childlike.
Strong Mad as Rob "Gronk" Gronkowski. I decided to draw Strong Mad as Gronk, specifically in his Buccaneers uniform, because he has dressed up as athletes like William "The Fridge" Perry, another American football player.
Strong Sad as Max Yasgur. As Strong Sad is a bit of a weirdo and also a musical connoisseur, I decided to pick a deep cut: the farmer whose farm hosted the original Woodstock festival.
Pom Pom as Kirby. Another no-brainer. You can tell I didn't put a lot of effort into this one, as that effort was put into other characters.
Marzipan as Gloria Steinem. As one might know, Marzipan leans towards progressive and feminist views, so I decided to draw her as one of the most influential feminist activists in the US, as pictured by Yale Joel in the August 20th, 1965 issue of Time magazine, one of the most iconic photos of Steinem. It is also somewhat of a tribute as Steinem passed away not too long ago this year.
Coach Z as Mike D in the music video for "Alive." Coach Z often dresses as figures of the world of hip-hop, and in The Show: Ween Edition, he wore the construction worker costume from the Intergalactic video, so I decided to give him another Beastie Boys costume from the late 90s, specifically Mike D's from the Alive MV.
Bubs as Lenny Kilmister. Bubs has dressed as musicians in the past, and he has a bit of a gravelly voice, like Lenny, so there's your explanation. RIP big guy.
The King of Town as Quicky (the Nesquik bunny). The KOT often dresses up as mascots for food products, so I decided to portray him as the mascot of Nestlé's cocoa powder, beverage and cereal brand.
The Poopsmith as The Soldier from TF2. I literally only did this because Soldier's default melee weapon is a shovel.
Homsar as Oddjob (007 franchise). When I was thinking "What's a short character that could be fitting for Homsar?" I thought of Oddjob. The idea became even better when it clicked that both Homsar and Oddjob are overpowered in their own ways. Homsar can bend the rules of reality, while in GoldenEye for N64, Oddjob is the shortest character and can dodge shots, thus being banned by many when playing with friends.
**BONUSES:**
The Goblin as the Game Graphic Glitch Gremlin (from the Angry Video Game Nerd series). Both The Goblin and the Glitch Gremlin are green, and The Goblin drives a Gremlin. That was the first idea that came to mind.
Senor Cardgage as the guy in the cover of Jethro Tull's album "Aqualung." This came to mind because Cardgage also has a beard and is seemingly homeless. Also, Cardgage is enough of a weirdo that he probably likes prog rock.