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I am glad that astro was able to actually step in and give him something nice to dream about, even though that memory seemed to be bittersweet at best too and I will dissect it later. But the scene with different versions of cuphead playing Russian roulette is going to be my main yapping point in this post at least,

Also to clear up my yapping I am going to refer to the different cuphead by their ages range ( + brother) but young adult cuphead refers to the one in the suit while just cuphead is the one that is like current times (I know they would both be young adults, (I imagine young adult being probably early twenties if not like 18-19) but I gotta separate them somehow).

The first shot being of young adult is really interesting, and the fact that he seems so afraid of where he lands, which is a giant roulette table, and the outfit plus the fact that it seems very reminiscent of the king dice battle suggests that there was a brief time that cuphead worked for the casino, or at the very least, was at it for a long enough time to probably get recognised by a few people. Which likely lead to a fight breaking out and who fucking knows how that ended, but if his mind is supplying him with that memory right after falling asleep while being in a lot of pain, probably means it didn't end too well for him. Something else is that young adult has diamonds for pupils, which is certainly odd but again suggests (to me) that he had some time being under the devil. My running idea is that young adult either is a actual time in cuphead's life when he was working at/visiting the casino, or that young adult represents what could have been if he and mug didn't do mercenary work. I'm leaning much more to the idea that it was an actual time in his life but the pupil thing kinda makes me think that young adult is not like an actual version of cuphead. Having young adult fall through the roulette table, only to land in this dark void and Immedently be shot and killed is so brutal and I love the imagery. And cuphead doesn't even look upset, he just seems bored, like he was waiting for this to happen with annoyance.

Cup seemingly snaps out of this little daze and we pan out to see three other figures (and young adults dead corpse on the ground) which are all in handcuffs and the other three have hoods on, like you would do leading a criminal to an execution. Young adult didn't have a hood and neither does cuphead. Anyways cup goes to pull one of the hoods off of the one behind him, which is kid, and blood comes pouring out from the bag, soaking kid in it. Kid looks up at cuphead and is crying and this is a fucking call back to chapter one right after cup got shot, mug started having a memory of when he lashed out at cup and kicked him out to go get the contracts himself. Time seemingly passed and mug was tweaking out, anyways the scene ends with him opening the door to see cuphead, covered in blood and crying, and asking if mugman still loved him. Kid is crying and clearly scared and doesn't even say anything the whole time, just has his head bowed in seemingly defeat and the other three fight, I imagine this is probably supposed to be him after his first fight, shell shocked and unresponsive, the first actual break in cuphead's mental state. Which would lead him down the path of thrill seeking and self-destruction, probably chasing that feeling of the first life he took.

Teen interrupts cuphead and kid by ripping off his hood and announcing "it's okay! Don't worry, the fun part is coming!" Which I took as implying as his turn in the roulette game they seemed to be playing, each lined up for their turn to play the game of life and death. Teen's careless behaviour is probably him at his most "thrill seeking" phase, which I can assume he probably played this exact game a few times over the years to get a kick, if the idea of the 'winning streak', which was mentioned both in the prologue and here in this little sequence. My guess is that he probably played Russian roulette a few times and didn't die, leaving him with a winning streak which cuphead then mentioned later when Boris refused to shoot him, because in that moment he didn't know Boris, he did know if he was going to shoot, he was literally playing Russian roulette then and once again didn't die. Teen also throws a bit of a fit when brother skips him in line, seemingly upset that he didn't get a chance to risk his life again and get that little thrill when it comes to winning. Teen, to me, seems to be the first time cuphead probably played Russian roulette, or something similar, where his life was on the line but he lived and was upset about that. Teen is probably more a representation of cuphead's adrenaline junkie time when he would seek out trouble and extreme danger. But I like to think that everyone (minus brother) represents a specific event in cuphead's life so just roll with me.

Brother skips over teen and goes to immedently to shooting cuphead, which the barrel is empty, and he announces "Winner!". Interestingly, he isnt broken here and is showing up to cuphead (reminder that brother is a hallucination by Mugman that represents this idea of cuphead) which means that both him and mugman likely have a similar opinions of himself. Brother isn't bound in this shot, he doesn't have the handcuffs anymore and has a regular gun, not the straw gun. He also puts up zero fight when cuphead tries to take the gun, just kinda let's him take it and start firing it. Cuphead's chains also break once he takes the gun which is neat, and as he's trying to kill himself the gun is completely empty, the only bullet in there being used on young adult, so there's no bullet that comes and kills him. Cup gets pissed that the gun won't fire and tosses the gun to the void as he is now standing on a ledge with no bottom to the void below him in sight. The other three are gone and now cuphead is just with Astro, who seems so genuinely worried about him. Astro comments that cuphead's dreams are scary, which is fair because that Russian roulette scene was upsetting, and says he tried to bring cuphead to a place that would calm him, but that place turns out to be a fucking cliff. He is calmed by the idea of dying.

Not to get all personal but when I severely depressed one of the things that comforted me in the face of feeling like a complete fuck up, was the idea that none of this mattered because one day I'm going to die. The scene with him sitting on the edge, staring down into the void and astro mentioning that this place "calms" him, I can't help but think it's the same thing. Repeatedly in motm cuphead is shown to have zero self preservation instincts, throwing himself into as much danger as he could before he finally actually dies because he sees himself as a massive fuck up. So of course he is comforted by the idea that someday he won't be a bother to everyone around him, especially mugman.

Are you sure? Okay, yapping begins now

oooh the shippers got FED with this episode, I think it was a really beautiful way to end the show and I'm so fucking happy Caine got to be happy

That being said I have a few.... critiques, Jax abstracting off screen felt a little like a cop-out, I think it could have worked a little better with no narration by Pomni, where instead it was just a hard cut to him being abstracted, or show him abstracting if you wanted to keep the narration. Also I LOVE the in his mind scene, great part of storytelling, I do wish that his death was more... fitting? Just getting flash banged felt almost silly and like a 'oh shit we need to end this scene' instead of a proper send off. Also I wish there was an explanation for why the circus finally got back to colour? Did the people do that or was that Caine coming back, how did Caine get out?

My only other major issue with the episode was that Pomni saying what everyone's life was like in the real world at the end felt a little weird, I think it would have worked better with everyone narrating their own life but that is personal opinion.