Thorin Oakenshield in the context of "Gimli (Middle-earth)"

The Hobbit is a trilogy of fantasy adventure films directed by Peter Jackson. The films are subtitled An Unexpected Journey (2012), The Desolation of Smaug (2013), and The Battle of the Five Armies (2014). The films are based on J. R. R. Tolkien's 1937 novel The Hobbit, but much of the trilogy was inspired by the appendices to his 1954–55 The Lord of the Rings, which expand on the story told in The Hobbit. Additional material and new characters were created specially for the films. The series is a prequel to Jackson's The Lord of the Rings film trilogy.

The screenplays were written by Fran Walsh, Philippa Boyens, Jackson, and Guillermo del Toro, who had been chosen to direct before his departure from the project. The films take place in the fictional world of Middle-earth, sixty years before the beginning of The Lord of the Rings and follow hobbit Bilbo Baggins (Martin Freeman), who is convinced by the wizard Gandalf the Grey (Ian McKellen) to accompany thirteen Dwarves, led by Thorin Oakenshield (Richard Armitage), on a quest to reclaim the Lonely Mountain from the dragon Smaug (Benedict Cumberbatch). The films expand upon certain elements from the novel and other source material, such as Gandalf's investigation at Dol Guldur which leads him to the Necromancer, and the heroes' pursuit by the orcs Azog and Bolg, who seek vengeance against Thorin and his kindred.

Smaug (/smaʊɡ/) is a dragon and the main antagonist in J. R. R. Tolkien's 1937 novel The Hobbit, his treasure and the mountain he lives in being the goal of the quest. Powerful and fearsome, he invaded the Dwarf kingdom of Erebor 171 years prior to the events described in the novel. A group of thirteen dwarves mounted a quest to take the kingdom back, aided by the wizard Gandalf and the hobbit Bilbo Baggins. In The Hobbit, Thorin describes Smaug as "a most specially greedy, strong and wicked worm".

Critics have identified close parallels with what they presume are sources of Tolkien's inspiration, including the dragon in Beowulf, who is provoked by the stealing of a precious cup, and the speaking dragon Fafnir, who proposes a betrayal to Sigurd. A further source may be Henry Wadsworth Longfellow's 1855 poem The Song of Hiawatha, where Megissogwon, the spirit of wealth, is protected by an armoured shirt, but whose one weak spot is revealed by a talking bird. Commentators have noted Smaug's devious, vain, and proud character, and his aggressively polite way of speaking, like the British upper class.

Bilbo Baggins (Westron: Bilba Labingi) is the title character and protagonist of J. R. R. Tolkien's 1937 novel The Hobbit, a supporting character in The Lord of the Rings, and the fictional narrator (along with Frodo Baggins) of many of Tolkien's Middle-earth writings. The Hobbit is selected by the wizard Gandalf to help Thorin and his party of Dwarves reclaim their ancestral home and treasure, which has been seized by the dragon Smaug. Bilbo sets out in The Hobbit timid and comfort-loving and, through his adventures, grows to become a useful and resourceful member of the quest.

Bilbo's way of life in the Shire, defined by features like the availability of tobacco and postal service, recalls that of the English middle class during the Victorian to Edwardian eras. This is not compatible with the much older world of Dwarves and Elves. Tolkien appears to have based Bilbo on the designer William Morris's travels in Iceland; Morris liked his home comforts but grew through his adventurous journeying. Bilbo's quest has been interpreted as a pilgrimage of grace, in which he grows in both wisdom and virtue, and as a psychological journey towards wholeness.