Aside from being a plentiful source of low grade calamari, Giant Squid are just as appetisingly useful for their role as Sea Monsters roaming the deep, attacking boats full of Cutthroat Island extras and being an all round menace to the high seas.
As a real life species, giant squid are believed to have inspired Norse tales of the Kraken and as one of The Oldest Ones in the Book had a lot of overlap with the epic Kraken and Leviathan. After Jules Vernes's Twenty Thousand Leagues Under the Sea, the Giant Squid became a much more of a monster in the vein of any other "Gigantic Animal" monster: much more explicitly a larger version of something already known, scientifically unstudied but explanable and belonging to a realm not yet fully discovered, in this case, the depths of the sea.
Being mostly tentacle, the Giant Squid has a variety of ways in which it may be depicted on screen. You might see only the tentacles, perhaps the top of the head occasionally peaks out of the water. A full body shot may be a climatic reveal and seeing the beaked mouth may be reserved for the death scene of some poor sucker being slowly dragged into it. Very often the tentacles almost seem to act as their own monster following the principle of only taking what is on screen as being real.
Authors, designers and illustrators not always being sticklers for accuracy, the trope Giant Squid includes giant octopuses and giant-sea-creatures-that-are-some-weird-hybrid-of-squids-and-octopuses, as well.
Subtrope of Sea Monster, see also Giant Enemy Crab and Everything's Squishier with Cephalopods.
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Films — Animation
The sequel to Disney's Peter Pan replaced the tick-tocking crocodile with a giant orange octopus which made popping noises.
Films — Live Action
The Kraken from Pirates of the Caribbean. Though far bigger than any real squid (thereby really earning its Kraken title) it still is very specifically squid in design from its tentacles to its eyes and beak.
Did it really have a beak? All we see is a giant maw full of long sharp teeth... Which Cpt. Jack Sparrow promptly jumps into.
Wake of the Red Witch, a black-and-white movie based on the novel "Toilers of the Sea", featured John Wayne wrestling with and killing a giant octopus that had carried off a native diver minutes before.
Reap the Wild Wind featured John Wayne fighting and being killed by a rather silly-looking (but technologically impressive for the time) giant squid. It was made several years after the above movie. Perhaps the squid was avenging its cephalopod brother?
Roger Corman's first film was Monster from the Ocean Floor, and featured a female marine biologist vindictivly hunting a giant squid.
Beneath the 12 Mile Reef has a giant human attacking octopus
Mysterious Island and It Came From Beneath The Sea were both Ray Harryhausen animated movies with giant killer cephalopods in them. In It Came from Beneath the Sea, it is a giant radioactive octopus and features as the main threat. Mysterious Island meanwhile feature what appeared to be either a giant nautilus or ammonite which attacks the castaways when they're exploring the sunken pirate ship.
Voyage to the Bottom of the Sea has a gigantic octopus in it which attacks the Seaview. Also, an actual giant squid earlier attacked the divers repairing the transatlantic phone line on the ocean bottom.
What are initially believed to be numerous worm-like creatures in Deep Rising that infested the ship and consumed the entire crew and its passengers actually turn out to be the tentacles of an extremely large squid-like monster at the end.
Boga Ten in Road to Bali.
In the Lord of the Rings films the Watcher in the Water was decidedly squid-like, with bits of octopus thrown in for good measure. In the books the description is a bit more vague but still retains most of the Giant Squid properties.
The Walt Disney version of Twenty Thousand Leagues Under the Sea prominently featured a giant squid that Kirk Douglas went against mano a mano (a mano, a mano, a mano...) with a harpoon.
To be elaborate on Twenty Thousand Leagues Under the Sea, the crew of the Nautilus (and Ned Land) fight a giant squid that has wrapped itself around the submarine. It is the most recognisable point after Nemo and the Nautilus themselves and is a standard fixture in any adaptation.
Seen as the cover morph in The Exposed, the twenty-seventh book in the Animorphs series. Rachel's shown as the morpher, but the whole team morphs squids in the book.
The giant squid from Harry Potter. It seems to care about the students, as on one occasion Fred + George are seen tickling it, and on another it puts a first year who had fallen into the lake back into the boat.
Michael Crichton's posthumously published Pirate Latitudes features two encounters with what is presumably a giant squid, which the characters call a "Kraken". The first one doesn't do much and is quickly forgotten. The second one is strangely aggressive, grabbing crew members and flinging them overboard. It also, for some reason, has bioluminescence.
Another Chricton novel, Sphere, also features a giant squid as a manifestation of a character's mind.
The narrator of Moby-Dick has an encounter with a giant squid:
Almost forgetting for the moment all thoughts of Moby Dick, we now gazed at the most wondrous phenomenon which the secret seas have hitherto revealed to mankind. A vast pulpy mass, furlongs in length and breadth, of a glancing cream-color, lay floating on the water, innumerable long arms radiating from its centre, and curling and twisting like a nest of anacondas, as if blindly to clutch at any hapless object within reach. No perceptible face or front did it have; no conceivable token of either sensation or instinct; but undulated there on the billows, an unearthly, formless, chance-like apparition of life.
As with a low sucking sound it slowly disappeared again, Starbuck still gazing at the agitated waters where it had sunk, with a wild voice exclaimed — "Almost rather had I seen Moby Dick and fought him, than to have seen thee, thou white ghost!"
Peter Benchley's Beast, later adapted into a film starring William Peterson called The Beast, could roughly be described as Jaws with a Giant Squid (especially since Benchley wrote Jaws) with the giant squid attacking boats after foolish mankind overfished its normal prey and accidentally killed its young. Mankind's hubris concerning nature leads to him getting attacked by a wild creature? Naaaawh!
Artemis Fowl is attacked by a giant squid in The Atlantis Complex.
In the seventh James Bond novel - Dr. No - the title character puts him through a torture labyrinth ending with an apparent escape only to be attacked by a giant squid. Improbably, Bond wins.
In one story of Prince Valiant, the epynomous hero is trapped above a large, deep pool with an enourmous octopus at the bottom trying to reach him. In another story, he is at sea with a small crew in a boat and is attacked by a giant squid.
In Pat Murphy's Adventures In Space And Time with Max Merriwell, Weldon Merrimax is killed by a giant squid.
Live Action TV
A really, really Giant Squid is worshipped as a god on a planet where the Doctor and Romana seek the Key to Time in the Doctor Who serial The Power of Kroll.
One episode of The Sean Cullen Show had a giant squid take over Sean's basement. It eventually kidnapped William Shatner and fell through a wormhole. Sean sang about it.
The Jonathan Coulton song "I Crush Everything" is sung from the perspective of a giant squid. It suffers from extreme loneliness, because (as the title hints) it can't touch anything without dragging it down to the bottom of the sea and destroying it. And it really hates dolphins. So, sad cephalopod.
The New World of Darkness has the Leviathan, the Kerberos of the Sea of Fragments. It's actually only a guess that it's a cephalopod based on the fact that it has tentacles — it's too huge for anyone to ever see what it really looks like.
Dystopian Wars takes this up to eleven - the Empire of the Blazing Sun have the Ika class Mechanical Squid - a gigantic robotic squid large enough to grab and drag down the largest warships into the briny depths.
One of the largest squid-like entities in the game RIFTS is the Lord of the Deep. Nobody knows if it really is squidlike, as only its tentacles are ever seen - its body is deep within the Mariannas Trench. Said tentacles are several MILES long, and thick enough to pose a threat to the ultratech BATTLESHIPS of RIFTS Earth.
Dungeons & Dragons has intelligent, evil Kraken. There's also stats for a perfectly mundane giant squid and giant octopus.
Munchkin has Squidzilla as one of its monsters. As the name implies, it is huge.
One of the optional ship battles in Skies of Arcadia is against a giant flying squid.
In Command & Conquer: Red Alert 2 the Wacky Soviets have giant squid that can drag enemy ships down to the briny depths. Too bad they traded those in for war bears in part 3.
One of the bosses in Resistance 2 is a huge, many-tentacled Kraken.
The giant pink squid thingy Krusher from Sly 3: Honor Among Thieves starts off as a boss fight before the Guru manages to talk it into temporarily joining you. You later control Crusher to defend Bentley by smashing pirates in a fashion in a scene that is best described as "Giant Squid Bongo with a Body Count".
One of the recurring enemies in Super Mario Sunshine is a giant squid with a cork in its mouth that sprays polluting ink everywhere.
The final Bonus Boss of Warship Gunner 2 is a giant squid that can sink ships with a blast of high-pressure ink or lasers. But it's a giant, flattened and dried squid.
The Endless Ocean games both feature giant squids in their respective abyssal zones. The second game also has the giant squid's baby, Kraken Jr., who's only a couple of feet long and amazingly adorable for a squid.
Even though it looks more like an octopus, Lusca from City of Heroes probably counts. There's no way to gauge how big it is, since you can't see the whole thing, but the amount of tentacle that you can see looks to be around 30 feet or more.
In Assassin's Creed II Ezio goes searching for the Assassin Seals that unlock the Armor of Altair, he can come across what appears to be a giant squid twice in the same area. Once he pulls on a lever and watches the water, he can see the dark figure swim past menacingly. If he pulls the lever again and waits, the squid will use a tentacle to attack Ezio and fail. If Ezio falls into the water at any moment, however, the squid will not come to attack him at all.
In Wakfu, a giant black squid kralamoure is protecting Oma Island by destroying in its tentacles any ship coming too close. It is in fact the form chosen by an ancient shapeshifting dragon.
The Garfield Show had a giant squid terrorizing the city's sewers. And it likes donuts.
The Giant Squid... and Colossal Squid. Yes, they do exist. While a few stories circulate of boat being attacked by large squid, these creatures are mainly deep-water dwelling creatures, that mostly eat smaller prey. There have been reports of Giant Squid toothmarks on Sperm Whale skins which indicate that the two species regularly fight each other, but since Sperm Whales actively hunt them, these wounds may have been inflicted in self defense.
Meanwhile, the largest octopus in the ocean is the Giant North Pacific octopus, with an arm-span of seventeen feet. There is not, as far as most scientists are concerned, any octopus of giant squid-sized proportions or whale-sized proportions, as urban legend seems to state.
The Humboldt squid, while not a large squid (5-foot long mantle) best fits this trope in its behavior. In California and Baja, where the squid are fished for, it's gained a nickname amongst the fishermen. Diablo rojo, which means "red devil". It does not sink boats, but when feeding or being fished up, they are extremely aggressive. Their beaks are too weak to break bones, but their strong arms have sharp teeth which can rip through skin and most wetsuits. They have also been known to attack underwater cameras and will eat other wounded Humboldts. However, outside of feeding and being fished, they have also been observed to be calm and curious, so their behavior is a subject of debate. Regardless, underwater cameraman Scott Cassell—who made a career filming them—won't go in the water with them without wearing a chainmail wetsuit.
Tusoteuthis, a distant ancestor of the modern-day vampire squid that generally ranged from 20-35 feet, was a fairly common denizen of the Cretaceous-era Kansas seas. Of course, given the nature of those seas, they were actually pretty low on the food chain. Fossil evidence shows that they were preyed upon by massive predatory fish, and it also stands to reason that they were regular prey items of mosasaurs. It says something about how nasty those seas were when a giant cephalopod was actually one of the less-threatening of the many predators roaming them.