Grim Matchstick bears an appearance similar to a typical dragon character from the game's time period.
He a fairly large, slightly chubby, European dragon with a very simple design. He has lime-green scales and a light-amber underbelly (lacking segments) that starts of at his distinct, beak-like muzzle. He has large pac-man eyes, no visible eyebrows (minus an indentation) and featureless ears on his head.
Grim has two large fangs resembling buck teeth and has a tongue that can extend like that of a frog, allowing his flame minions to walk across (similar to the famous red carpet method).
On his shoulder blades that, he has average-sized, bat-like wings, the same color as his scales, that are flexible and can shape into arms (similar to actual bats), as seen in his intro, where he forms them into hands with fingers. His limbs are rather small and stubby with four fingers on each hand, two toes on each foot, and silver claws/talons. He also milk-white spikes running all the way down his spine (like many other dragons in popular culture), and he has a very long tail, which he uses like a baseball bat to swat his victims away.
When Grim reaches his third phase, he grows to more heads on his shoulders that look exactly the same as the original's head, which morphs into a red flame-thrower with a gold fire blower and gasoline tube.
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 with a slightly child-like demeanor who likes to have fun, which is also implied 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, a hanging tongue, and downed ears on 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.|
|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|
- Grim's first name "grim" means forbidding, uninviting, and/or morbid. Ironically enough, Grim is essentially the opposite of his name's true meaning in terms of physical appearance and personality.
- While not apparent at first, his appearance is ever so slightly reminiscent of that of the Disney character, Elliott, the bubbly, sweet-natured dragon from the classic 1977 Disney film, Pete's Dragon, and it's reboot from 2016 (released a year before the game's debut).
- Both dragons have a manly green color palette (emerald-green for Elliott, lime-green for Grim), small, cow/deer-like ears, small, bat-like wings on their shoulder-blades, and are rather chubby in appearance (although Elliott's stomach is bigger than that of Grim's).
- The similarities are more apparent in his reboot counterpart, specifically the scene leading to the climax, as well as in the original.
- In the original film, Elliott spends most of the film fighting of Dr terminus, Hoagy, and the Gogans to defend himself and Pete from getting seperated, captured and/or killed. And In the reboot, he fights off Gavin and his many accompanies to prevent himself from getting caught.
- Similarly enough, Grim spends the entire battle fighting off Cuphead and Mugman to defend himself, his soul and his contract.
- However, despite the similarities, Elliott and Grim have a good deal of differences between one another.
- Elliott has a very large chin, a mint-green, segmented under-belly that begins only under his chin, tufts of pink hair on his head, ears, and tail, and forest-green spots on his body. He also lacks the ability to grow more heads or shoot eye ripple (although his eyes are seen changing color) and is incapable of speech (minus several animalistic noises such as clicks, scats, and growls). He also can become invisible, his fire-breathing is much more realistic, and he (most likely) has bright blue eyes.
- Grim, on the other hand, has a more beak-like muzzle with (presumably) no chin, a light-amber stomach that starts on his muzzle and lacks segments, has no spots on his body, and is completely hairless. He is also able to talk (complete with uncontrollable stuttering) and grow spare heads and shoot eye ripples (similar to hypnotism), and his fire-breathing is far more cartoony (considering the old-times style of the game itself), complete with a parade of literal fire people. He also can't make himself invisible and apparently has no genuine eye color.
- Grim's personality matches that of the Dragon from The Reluctant Dragon, as both characters are wanting to prove that they are friendly and gain acceptance into society among their peers.
- 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.
- Grim's facial stucrture, complete with a pointed muzzle, bears a small resemblance to that of Maleficent's dragon form the 1959 Disney film, Sleeping Beauty.
- 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 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 and it's 2010 film adaptation from Dreamworks animation (where toothless never speaks).
- 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.
- 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.
- 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.