Gloomtail

"WHAAAAAAAAAAAAAAAAT?!? You destroyed my precious younger sister?!? I wondered why she hadn't written recently…"

- Gloomtail

Gloomtail is the middle sibling in the "tail" family in Paper Mario: The Thousand-Year Door. He is the older brother of Hooktail and the younger brother of Bonetail. Upon hearing Mario's partners say they defeated his sister Hooktail, Gloomtail vows to destroy Mario and company. He lives in the Palace of Shadow and guards the Star Key, which is needed to unlock the pedestals in the Riddle Tower. Mario and company had to defeat Gloomtail to get the Star Key.

Gloomtail is much stronger than his sister. He attacks by breathing poison on Mario and his partner, this takes at least ten turns to wear off, and stomping or chomping the character in front. His Earthquake move can be dangerous, but it doesn't work on Vivian and Flurrie. He can also charge up for his signature and strongest attack: his Megabreath move, which does up to 16 damage.

Quotes
For a full list of quotes, see here

Trivia

 * Gloomtail is the only dragon boss in Paper Mario: The Thousand-Year Door that does not have a Super Paper Mario equivalent.
 * The room Sir Grodus is fought in is directly below Gloomtail's room, which would mean that Bowser was in Gloomtail's room when he fell through the floor.
 * Bonetail has the same default attack and defense stats as Gloomtail.
 * Gloomtail's room is similar to the spike room in Hooktail's Castle; if the player uses Bobbery at the right end at the wall, a room will open and an Ultra Shroom and a Jammin' Jelly can be collected.
 * Gloomtail has the fourth strongest enemy attack in the entire game. His Megabreath can do 16 points of damage, 2 points higher than the Shadow Queen's Megawave attack. However, if the Shadow Queen charges up (Increases attack and defense) and then charges up for the Megawave, her attack does 17 points of damage. The Amazy Dayzee has an attack power of 20, which can deal great damage to Mario and his partner. The highest attack power belongs to Marilyn's Slap attack, which can do 7 points of damage, but when charged up, she can deal up to 21 points of damage.
 * If Mario brings Flurrie, Yoshi, Vivian or Bobbery when seeing Gloomtail -- partners that were not available during the battle with Hooktail -- they will confuse him for Hooktail, going off on several descriptions Mario told them about offscreen.