Cuphead is known for how ridiculously difficult its boss fights are. But what if we put every boss in a ridiculously difficult situation? Ya know, give ‘em a little taste of their own medicine? Here’s every boss in Cuphead ranked by how good of a first impression they’d make on my parents.
And to be clear, for each boss, it is to be assumed that I’ve been dating them for 4 months, and that my parents don’t know anything about them beforehand.
#35: Chef Saltbaker
There simply wouldn’t be time for my parents to form an opinion of Chef Saltbaker, as he would kill all of us and eat our souls immediately.
#34: Beppi the Clown
From the mere moment Beppi waltzes in, my parents would be screaming for their lives. He’d walk around the house like he owns the damn place, probably hop on the table and start dancing, all while not acknowledging any of the stern warnings my parents give him. Beppi doesn’t give a flying fuck.
#33: Mr. Chimes
You aren’t even worth my damn time, Mr. Chimes. Go reflect, and maybe learn to do anything other than banging those annoying ass cymbals all the time.
#32: Glumstone the Giant 
Glumstone would burn my house down. I don’t think this guy cares about anything but spreading terror and sadness and destruction.
#31: Phantom Express
“Mom, dad, I’d like you to meet the evil train chock-full of ghouls and skeletons I’ve been dating.” There’s not many ways this could go too well.
#30: Sally Stageplay
After all the janky high school theatre productions I made them go to, I don’t think my parents could resist beating Sally Stageplay to death immediately upon seeing her.
#29: Werner Werman
I’m trying hard to imagine a scenario where this guy doesn’t get eaten alive by our dogs before he can even step foot into the house. I’m sorry Werner, but dude, you’re fucked.
#28: King Dice
I get the feeling we would have to meet in a neutral setting for this one, like a coffee shop. Something just tells me my parents already knew King Dice long ago, but haven’t seen him in decades. My parents would feign politeness to King Dice to please me, but I’d pick up on the tension in the air fairly quickly. How did they know each other? What do they know that I don’t? I don’t think these questions will ever be answered.
#27: Hopus Pocus
Hopus Pocus would charm the shit out of my parents. I mean, who doesn’t love magic tricks? He’d keep us entertained all night, and after he left, we’d look around and realize that he stole every last piece of furniture in our home.
#26: Pip and Dot
My dad would love Dot, but hate Pip, while my mom would love Pip, but hate Dot. This would start as a playful disagreement, but ultimately result in a really heated argument where items get thrown. Pip, Dot, and I would just have to hang out in my childhood bedroom until it’s all over.
#25: Chips Bettigan
Chips Bettigan would kill any sort of pre-existing vibe, and I’m not even sure he’d give a shit about meeting my parents. He’d just raid our fridge and leave.
#24: Mr. Wheezy
Aw, I just know Mr. Wheezy would be so nervous. I’d calm him down and reassure him that my parents are chill and I know he’s going to do great. Then we’d enter and he’d accidentally knock over a vase and run away, never to be seen again.
#23: Hilda Berg
Hilda Berg would do great at first, until she has one awkward interaction with my dad and then turns into the fucking moon in my living room.
#22: Djimmi The Great
This guy is almost too cool. Look at that dope ass sherlock pipe! But my parents would just keep asking him to grant their wishes, and I’m not sure Djimmi would like being bombarded with demands like that. So even though it isn’t exactly his fault, Djimmi’s going to have to be low on the list. Sorry!
#21: Ribby and Croaks
My parents would be so excited to determine what exact species of frog Ribby and Croaks are. Then, as my parents are distracted – and since they’re somehow able to do this – Ribby and Croaks would morph into a slot machine, and give both my parents a gambling addiction. Classic hook, line, and sinker.
#20: Mangosteen
I can’t shake the feeling that he’d just keep asking my parents weird, uncomfortable questions though. Like he’d probably try to make them cry, like the sadistic fuck he is. What a terrible presence. Fuck you, Mangosteen.
#19: Esther Winchester
Esther never stops smiling. Even when her entire body turns into sausage links. That has to be unbelievably painful, right? For all of your body and internal organs to just turn into sausage links? You have to be a sick fuck to smile through all of that. My parents would be very disturbed.
#18: Baroness Von Bon Bon
It’d probably go fine if not for the fact that Bon Bon would probably bring her whole gaggle of numskulls and goofs with her too. Isn’t she some kind of royalty? I don’t even know why she hangs out with those weirdo fucks.
#17: Mortimer Freeze
He’s pretty chill, and seems like a perfectly decent person, but he wouldn’t really make a lasting impact. He just needs to do his own thing. There’s already the Ice King from Adventure Time, and that Snow Miser guy too. C’mon Mortimer, you’re like the 34th most significant cartoon guy with ice powers.
#16: Phear Lap
The most interesting thing about this guy is that he wears a green visor, and once he milks that for 5 minutes of conversation, he literally has nothing else to offer.
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