Cressida Cowell’s 2003 book How to Train Your Dragon spawned 11 sequels following further adventures of Hiccup and Toothless. Naturally, then, the movie adaptations of those books (which took great liberties with their source material) could not be confined to just one feature film. The original How to Train Your Dragon from directors Chris Sanders and Dean DeBlois launched in March 2010 and proceeded to spawn two animated sequels and one live-action remake (plus three TV shows). With the live-action remake of How to Train Your Dragon creating a storm at the box-office, and a live-action redo of How to Train Your Dragon 2 on the way, it doesn’t look like Hiccup and Toothless are vanishing from the big screen anytime soon.
How do you stick around so long in the cinema scene? Quality helps, certainly, and the How to Train Your Dragon franchise is rife with that element. These animated films especially are some of the most acclaimed productions to ever come out of DreamWorks Animation. Ranking the four feature-length Dragon installments underscores the artistry making this saga such an enduring staple of modern cinema.
4) How to Train Your Dragon (2025)
DeBlois, making his live-action directing debut with the 2025 redo of How to Train Your Dragon, demonstrates competency transitioning to another medium of storytelling. His use of practical sets and natural locations for the film’s backdrops are a great touch. Toothless’ cute design and John Powell’s score also remain tremendous. Otherwise, though, this flesh-and-blood take on Dragon is a bit of a shrug. Not offensively bad like the worst live-action Disney remakes, but also an uninvolving beast, too slavishly devoted to the initial animated feature to uncover its own personality. Strangely cramped framing and weird-looking attempts to translate heightened cartoon characters into live-action further dilute the proceedings.
3) How to Train Your Dragon 2
How to Train Your Dragon 2 tries biting off a lot more than it can chew as a 102-minute movie. That means it’s an excitingly audacious animated family movie sequel, but it also means Dragon 2 features undercooked elements like extraneous comedic elements involving wacky teenagers like Fishlegs or Snotlout. Otherwise, though, Dragon 2 is a gorgeously animated production featuring truly spectacular voice-over performances (Cate Blanchett especially shines as one of the film’s new characters) and impressively dark storytelling impulses. A willingness to temporarily make Toothless a murderous villain, for instance, runs counter to the sanitized toyetic tendencies of so many American animated features. Though not the equal of its predecessor, How to Train Your Dragon 2 is no hollow cash grab.
2) How to Train Your Dragon: The Hidden World
There’s a welcome sense of finality to How to Train Your Dragon: The Hidden World that lends it some extra emotional power. This is not another adventure in a ceaseless franchise but rather a farewell, concretely showing why dragons and humans can’t live together. It’s also a title rife with vividly fun animation, particularly in depicting Toothless and the Light Fury’s physicality in their courtship. Grand detours into pathos and a memorably devious villain, deliciously voiced by F. Murray Abraham, further enhance The Hidden World’s joys. It’s hard to imagine anyone walking away from How to Train Your Dragon: The Hidden World and not feeling it satisfyingly wraps up the Hiccup saga.
1) How to Train Your Dragon (2010)
There was no real mold in 21st-century feature-length computer-animated American movies for what How to Train Your Dragon was trying to do. Rarely did these films focus on teenagers or dragons. Meanwhile, the more dramatic dialogue-free impulses ran counter to post-2001 titles full of snarky pop culture references popularized by fellow DreamWorks film Shrek. That lack of immediate modern ancestors, though, let Dragon soar to the beat of its own drum. Rather than mimicking what audiences had already seen, the saga of Hiccup and Toothless changing the world with their friendship was utterly unique.
Sanders and DeBlois transferred to Dragon their gifts from Lilo & Stitch of mixing heightened fantasy with raw depictions of familial strife without missing a beat. There’s an emotional rawness to the most challenging father/son moments between Hiccup and Stoick the Vast, while scenes of Toothless soaring across the sky are truly glorious to witness. Powell’s score is also a mesmerizing accomplishment, as are the memorable dragon designs. Refusing to bow to “normal” traits of typical American animated movies served How to Train Your Dragon so well that it’s still inspiring remakes and new fans to this day.
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