Cuphead Week!

Official blog for Cuphead Week! An event that happens twice a year! (During the last week of June for the DLC and the last week of September to celebrate the anniversaries of Cuphead's Main Game and its DLC through cool artwork!) Blog run by @orangeleftyart Disclaimer: This blog is not affiliated with Studio MDHR or any other creators of Cuphead!

[cuphead-week]

Now presenting: The Cuphead Week September 2025 Calendar!

The prompts are the same as last year, but since only a few people could participate last year I decided to recycle them :)

Remember: You do not have to do all of the prompts to participate! And it’s okay if you post something late!

I will be try to reblog Cuphead Week arts here so please tag me @cuphead-week when you post them! (It’s easier than searching through the tags)

Please reblog this post to get it out to more people! I wanna see if we can get more participants this year!

And you can create anything based on these prompts! (Art, crafts, 2D or 3D, digital or traditional, writing, music, etc!)

If you have any questions, please DM me! <3

[orangeleftyart]

Happy 8th Anniversary to Cuphead!

Unfortunately I’ve been so busy lately that I couldn’t draw much in time for today, but this game genuinely means so much to me. Even 3.5 years after I found it! And the friends I’ve made because of it… yeah 🫶

[dawlotte]

Cuphead Week Day 7 - Victory

HAPPY 8TH ANNIVERSARY, CUPHEAD!!! ☕🎉

Without this franchise I don't know where I'd be right now, honestly. I adore this franchise with all my heart, and I can't be more grateful for the awesome mutuals I've made who share the same love. This challenge was just as fun to do as last year. I'll also be posting more Cuphead art daily throughout October- or rather, INKtober!

[dawlotte]

Cuphead Week Day 6 - Inkwell Hell

[dawlotte]

Cuphead Week Day 3 - Isle 3

[dawlotte]

Cuphead Week Day 2 - Isle 2

I don't have much time to draw every Cuphead Isle character digitally sadly, so not all Cuphead Week art will be made digitally. Isle 4 and the last day will most definitely be digital, and I'm gonna be sure to make the last one as best as I can. Hope you all enjoy this regardless.

[dawlotte]

Cuphead Week Day 1 - I Isle 1

[dawlotte]

Cuphead Week Day 4 - Isle 4

[dawlotte]

Cuphead Week Day 5 - The Cup Trio

[orangeleftyart]

Happy 3rd Anniversary to the Cuphead DLC!!

The Cuphead DLC will always have a place in my heart, it is truly so nostalgic and I have so many fond (and yet frustrating, lmao) memories of it. Also I like to think that the Cuphead DLC OST is PERFECT for summer time!! It will forever be on my summer playlists ;)

(Variations of this drawing under the cut)

[orangeleftyart]

10 Days of Cuphead DLC Days 6 & 7: High Noon Hoopla! and Doggone Dogfight

This is a sketch of Esther Winchester I drew last year :3

And this is a drawing from 2022

I put these two days together in one post cuz I forgor to post yesterday 😭

[orangeleftyart]

10 Days of Cuphead DLC Day 5 - Bootlegger Boogie!

this is a drawing from 2022 :3 I love bootlegger boogie the ost is such a banger

bonus! (also from 2022)

[orangeleftyart]

10 Days of Cuphead DLC Day 4 - Snow Cult Scuffle

This is a drawing of Mortimer Freeze from January 2023 :3

[cuphead-week]

btw guys it’s okay if you’re late for some of the days of the cuphead dlc drawing challenge! just pls tag me @cuphead-week or @orangeleftyart so i can reblog your arts!! :3

[orangeleftyart]

10 Days of Cuphead DLC Day 3 - Gnome Way Out

Gonna do sketches of bosses from now on until the last day lol

[blazeberrychaos]

Glumstone the Giant!!! Day 3 of the Cuphead DLC week!! @cuphead-week

This was my first time drawing glumstone and i gave him my own idea of his design :3

[blazeberrychaos]

6 hours this took me but Day 2 of the Cuphead DLC week thing @cuphead-week