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Rupert Giles was born in 1954 into an upper-class family in London, England. They had worked within the Council of Watchers for at least three generations; both Rupert's father and grandmother, Edna Giles, were also Watchers. Being a Watcher is a calling, much as being a slayer is, and Rupert's father told him his destiny. A rebellious youth, Rupert dropped out of his history degree at Oxford University when he was 21. He delved into dark magics and befriended a group of young people that delved into the dark arts for fun or money: Ethan Rayne, Philip Henry, Diedre Page, Thomas Sutcliff and Randall. Together, they summoned a particularly grostesque demon called Eyghon, who would eventually murder Randall. Rupert gained the nickname "Ripper" during this time. The past would later come back to haunt him in the second season episode, "The Dark Age". During this time, Ripper employed tales of demons and dark magics, and also claimed to be a founding member of Pink Floyd in order to impress girls, although he later admitted this was untrue. It is also possible that he delved into criminal activity, primarily stealing cars, but most likely for joyriding. ("Like riding a bloody bicycle" he says as he hot wires his car in "Dead Man's Party (Buffy episode)")

Following the death of Randall after Ripper, Ethan and the others failed to exorcise Eyghon, Rupert accepted his destiny of becoming a Watcher. According to the comic "Buffy the Vampire Slayer: Giles", his mentor was Archibald Lassiter. He also became "the curator of a British museum, maybe the British Museum" as Willow says ("Welcome to the Hellmouth").

Sunnydale

At the behest of the Watchers' Council, he traveled to Sunnydale, California and worked as the librarian at the local high school. There he met the current slayer, Buffy Summers, whom he began training. The library, a sort of command center for the gang, sat right above the Hellmouth.

As the Watcher, librarian and general authority figure, Giles often delivered exposition. He was a father figure to Buffy and an advisor to her friends Xander and Willow. His character was often portrayed as somewhat of a "straight man" and his "stuffy" Oxford sensibility served as counterpoint to the stereotypical Southern Californian characters and setting. He would make a "weird cluck-cluck sound with his tongue" when he is angry but "too English to say anything" ("Faith, Hope & Trick").

Giles shared with Kendra (season two) an appreciation for the obscure text and served as Faith's watcher for a few weeks (season three). After pressing the trigger that destroyed Sunnydale High and put him out of his job, Giles spent months unemployed before buying the local magic shop, The Magic Box, after its last owner was murdered. He brought up the difficult idea of killing Dawn when the group labored to find a way to defeat Glory, and when Buffy spared Ben's life, Giles decided he could not give Glory the chance to return. Telling Ben that Buffy was different from them, he suffocated Ben with his bare hands.

After Buffy sacrificed herself to save the world, Giles decided to return to England. On the very day he left, her friends resurrected Buffy. When he learned of this, Giles returned, but soon decided that his presence was preventing Buffy from assuming responsibility for her own life. He left again for his native England, moving to a place near Bath, where he worked with a powerful local coven.

A few months later, Willow's girlfriend Tara was killed by a stray bullet as Warren Mears attacked the Slayer. Willow, still recovering from an addiction to dark magic, suffered a relapse, killed Warren and attempted to kill his former partners in crime, before resolving to end humanity's pain by destroying the Earth. Giles teleported back to Sunnydale, wielding great magical power borrowed from the Coven. Knowing that Willow was too strong, Giles tricked her into draining him of his magics, which brought him near death. It also allowed Xander to reason with her as the good magic brought out her natural love and compassion, eating away at the evil within her.

Giles returned to England with Willow for her rehabilitation. A few months later, he brought potential slayers to Sunnydale to protect them from The First Evil and its Bringers. He had removed a few volumes from the headquarters of the Watchers' Council, which was soon afterward destroyed by an agent of the First Evil. After the First's plan was foiled by the destruction of the Hellmouth and of Sunnydale, Giles traveled to Europe with Buffy and presumably began rebuilding the Watcher's Council.

Shortly after Anthony Stewart Head's departure from the series, there was talk of a spinoff series from Buffy the Vampire Slayer for the BBC entitled Ripper. As of 2004 the project was dead, however in 2005 Joss Whedon said he was still trying to get it off the ground, "but the ground is kinda sticky."