Toothless is Hiccup Horrendous Haddock III’s dragon and deuteragonist in the How to Train Your Dragon franchise. Playful, inquisitive, and intelligent, Toothless is more Hiccup's best friend than his pet. He is extremely protective of his Viking soul mate and will stop at nothing to guard him from all harm. As the last known specimen of the Night Fury species, Toothless is indisputably special. He commands respect from dragons and humans alike.

Toothless made his Macy's Parade debut in 2013, alongside Snoopy, Spongebob Squarepants, Adventure Time with Finn and Jake and The Wizard of Oz, to promote the franchise's second film, How to Train Dragon 2. It took a grand total of 90 handlers to guide him from 77th Street to 34th Street. He made subsequent appearances in 2014, and 2015, where he promoted Dragons: Race to the Edge. He retired that same year. He returned in the 2018 parade, to promote the new installment in the How to Train Your Dragon franchise, How to Train Your Dragon: The Hidden World.