Cheery Littlebottom is a dwarf member of the Ankh-Morpork City Watch, introduced in Feet of Clay. Her name might come from the British nonsense phrase "Cheery Bum," a common misunderstanding of the refrain of the kitsch Italian song "Ciribiribin". Cheery's father was Jolly Littlebottom, and her grandfather was Beaky Littlebottom.
The Commander of the Watch, Sam Vimes, hires Cheery in Feet of Clay as a one-dwarf forensics team. As he says, "I want someone who can look at the ashtray and tell me what kind of cigars I smoke" (a reference to Sherlock Holmes). Originally trained as an alchemist, Cheery left the Alchemists' Guild to join the watch after she blew up the entire leadership of the Guild. She begins her career in the City Watch working in an old privy, but rapidly earns Vimes' trust and respect and is given what she needs when she needs it. Jingo credits her with the idea of using trained pigeons for in-city communication between Watch officers. By Thud! she is promoted to sergeant. Her expertise is invaluable in uncovering the plot o poison Lord Vetinari by the Dragon King of Arms who is Ankh-Morpork's chief Herald and Arthur Carry. the candlemaker. When hiring Cheery, Vimes says, "Cheery, eh? Good to see the old naming traditions kept up." This is a reference to the names of the Seven Dwarfs in Disney's Snow White film: Grumpy, Dopey, Sleepy, Bashful, Happy, Doc and Sneezy.
Cheery is somewhat atypical for a dwarf. She hates beer and dislikes being an axe-wielding homocidal maniac; she also hates gold. When first introduced, she is referred to as male because, for dwarfs, gender is not really important. Like all dwarfs, of both genders, Cheery has a thick beard, boots and iron helmet. Her femininity is a close secret - only Angua, with her nose, is able to tell Cheery's true sex. Once outed, Cheery embraced her gender and began adapting to the more forward-looking gender attitude in Ankh-Morpork. Throughout Feet of Clay she begins wearing make up and high-heels (welded on), slightly worrying Vimes and Carrot. She also elects to change her name to 'Cheri'. Like many others, Cheery had a strong hatred of werewolves on the belief that a werewolf ate one of her relatives and wears silver chainmail, which upsets Angua. When Angua rescues her and is forced to reveal her wolfish nature in the process, Cheery states that her relative being eaten by a werewolf was likely apocryphal.
When she goes back to Überwald as an open female she causes the same kind of reaction that gays created when first 'coming out' and clearly Pratchett is drawing parallels. However it isn't long before, she begins a cultural revolution and introduces two new pronouns - "she" and "her" - to the dwarfish language. Many detest her, calling her "Ha'ak", which is an extremely derogatory word in Dwarfish. She goes pale the first time she hears it, and both Detritus and Vimes (technically her superiors) are ready to begin war with those who utter the word in their presence: Detritus with an army of dwarfs on the way to Uberwald and Vimes with the whole of Dwarfdom when it's uttered by Albrecht Albrechtson deep in the mines of the Low King. However, many dwarfs are discovering that their 'sons' are dabbling in make-up and heeled boots and are "coming out" as female thanks to her.
In subsequent appearances, Cheery reverts back to her original name, though pronounces it 'Cheri'. She forms part of the expedition to Klatch in Jingo, and accompanies Vimes to Uberwald in The Fifth Elephant, where her open femininity causes some comment among the conservative dwarfs there. Her last appearance is in Thud!.