Grim Matchstick is a large, chubby green dragon with stubby limbs. He has flexible and shapeable wings, as seen in his intro, where he forms them into hands with fingers. He also has a huge tail, a large mouth with a long tongue, and completely white spikes on his back.
Grim Matchstick strives to spook people, making "ghostly" motions whenever the battle commences. He also stutters when speaking, as shown by his death screen lines. He happens to be a lighthearted and playful dragon who likes to have fun, which is also proven by his intro and his first phase death screen.
Interestingly, Grim is one of the only two bosses (the other being Weepy) in the game that doesn't actually want to hurt Cuphead and Mugman. He views himself as misunderstood and apologizes for being forced into putting the brothers in a hot seat if they lose to him in his second phase. He even suggests that the brothers should run away from him after he turns into a hydra in his third phase.
The battle takes place in the cloudy area above Grim's tower where there is no ground to suppress any kind of fall damage. Grim Matchstick introduces himself by making a spooky gesture with his wings and face, possibly in an attempt to look scary or intimidating.
"Don't m-m-m-misunderstand my flames -- I just meant fun and games."
—Grim Matchstick, Phase 1 Death Screen
In this phase, Grim mostly stays to the right side of the arena and damages the player/s with these attacks:
- Grim shoots ripples from his eyes, which consists of 3 ring-like projectiles, 4 after losing some health, at the players. The final ring of the beam can be parried.
- He can shoot large fireballs that travel in a wave pattern. He sometimes shoots two at the same time that crisscross each other, but only does this when he reaches a damage threshold.
He also uses his tail to attack by jabbing at the player(s) from the bottom of the screen. Getting hit by his tail can be avoided if players pay attention to the bottom of the screen and the sound of the attack, which is the sound of his tail wiggling.
After taking enough damage, he will slowly disappear from the right side of the screen and fly over to the other side, which can be seen in the background. He later appears on the bottom left and commences the second phase of the battle. Hitpoints = 660/629/684
In Expert mode, the clouds fly to the right of the stage instead of the left.
"Sorry, I didn't mean to put you in the h-h-h-hot seat..."
—Grim Matchstick, Phase 2 Death Screen
In this phase, Grim will send out a parade of marching fireballs that travel across his tongue, which he stretches out as a platform. The leader fireball and the grouchy fireballs do not jump and simply act as an obstacle. The grinning fireballs will jump either directly towards the player or to the right side of the screen (no matter the location of the player/s) in an arc trajectory, and try to damage the player(s). The fireballs will crouch facing left or right before leaping, telegraphing where they are going to jump. If the player stays to the left, or only dodges fireballs by jumping left, they will rarely have to worry about fireballs jumping in a random direction. Grim also shoots out smoke or fire from his nose. This will obviously damage the player(s) if they run into it.
After taking enough damage, Grim will retract his tongue while his eyes bulge out of his head, then promptly rears up and grows two more heads, becoming a three-headed dragon. Each of his heads makes comical laughing expressions and the background turns into a rainstorm. In Simple mode, however, he won't grow any extra heads and the battle will end instead. Hitpoints = 540/510/551
"One..two..three! You'd b-b-b-etter flee!"
—Grim Matchstick, Final Phase Death Screen
In the final phase, players now face a three-headed Grim in a rainstorm. Grim, along with his two other heads, shoot about 6 to 9 cluster fireballs at the player/s, which can be destroyed but clustered into four directions in a plus formation. Hitpoints = 5/5
After shooting a number of fireballs, Grim's middle head will morph into a flamethrower (if observed closely, it is the original head) and fire a stream of flames that go right down the middle of the screen two times in three seconds before returning to normal and repeating the same process.
Once the players manage to destroy enough of his remaining health, Grim will be defeated with an X mark on both eyes, opened tongue, and downed ears of all three of his heads. Hitpoints = 561/665
|Grim Matchstick activating and deactivating his peashot mode.|
|Grim Matchstick coughing out meteors.|
|Grim Matchstick using his tail for attacking.||File:Sfx level dragon tail appear.wav|
|Grim Matchstick dashing through the sky.|
|Grim Matchstick snorting out fire.|
|Grim Matchstick snorting out smoke.|
|Grim Matchstick's transformation.|
|Grim Matchstick defeated.|
|Normal Mode||Expert Mode|
- His appearance is ever so slightly reminiscent of Elliott from Pete's Dragon while his personality matches that of the Dragon from The Reluctant Dragon. He also bears a resemblance to Taro from The 7th Voyage of Sinbad which is one of the creatures animated via stop-motion by Ray Harryhausen.
- The fight is similar to the Mecha Dragon boss fight from Mega Man 2.
- Grim's second phase has fireballs with legs coming out of his mouth. These fireballs are possibly a reference to the similar-looking fireballs seen in Mickey's Fire Brigade and Elmer Elephant as well as Bimbo's Initiation.
- His final, three-headed form is presumably based off of King Ghidorah from the Godzilla franchise or the Hydra, a three-headed dragon from Greek mythology (though it is said that the Hydra have more heads than three depending on some interpretations of the mythology).
- In terms of old cartoons, Grim Matchstick's final form is based on The Calico Dragon from the 1935 cartoon of the same name.
- The rainstorm in the 3rd phase was reportedly influenced by the storm scenes in Disney's The Mad Doctor and The Old Mill.
- In the introduction to the fight, Grim Matchstick is seen using his wings to make a spooky gesture, rather than his hands.
- Grim's design is a reference to the dragon in The Twisted Tales of Felix the Cat.
- The castle in the background of the fight is actually a real-life model.
- Grim was one of the few sample bosses playable on the 2015 Demo.
- In the 2017 demo, Grim was the only one having no comment about the player's death.
- In the Old Testament, one of the stories describes a young Moses touching a plate full of embers and then sticking his hand in his mouth to cool it, causing him to scorch his tongue. Since then he heavily stutters, which might be a distant reference to Grim Matchstick's stuttering since he breathes fire.
- Grim's stutters may be also similar to Toothless, who is also a stuttering black dragon from the book series How to Train Your Dragon.
- The name "Grim Matchstick" is most likely a reference to Grim Natwick, the animator who originally designed Betty Boop.
- His last name is likely a pun, as matchsticks are used to create fire.
- Like his namesake, Grim Matchstick shares the same stutter with Grim Natwick.
- His first name is likely a reference to the Brothers Grimm who used dragons in their fairy tales such as The Two Brothers and The Singing Bone.
- Originally, Grim fired different colored balls from his eyes instead of the rings he shoots now.
- The player can skip his final phase when doing enough damage to finish him, ending him on his third stage knockout instantly without any transformation.
- In the intro for the final phase, one of Grim Matchstick's heads has two mouths, which is most likely an animation error.
- The splitting fireball in the final phase has three different way to split, the in-game version where it split in all four directions and the other two split in left/right and up/down, the latter two were scrapped very quickly as only the left/right way to split is programmed but the up/down way wasn't even programmed.
- In an interview, it was revealed that Grim Matchstick's 2nd phase was originally going to turn him into a tambourine and the fireballs would be replaced with music notes, but this idea was scrapped because they agreed that it didn't make sense.