29 Years Ago, ‘Buffy’s Wisest Character Got a Shocking Backstory that Redefined the Entire Series

Giles received an unnerving backstory in one of season 2’s most memorable episodes

In Buffy the Vampire Slayer, Halloween is the one night a year when monsters think it’s cliché to go out and torment the Hellmouth. As Buffy elegantly puts it: Halloween is “like, dead for the undead.” But 29 years ago, one evildoer decided to wreak havoc in Sunnydale on the one night no one expected. The result was an episode that explored the characters' deepest insecurities and gave the Scooby Gang an unexpected hero: Rupert Giles (Anthony Head), the fussy librarian who until then had served as Buffy’s moral compass and cheerleader. While he ended up saving the day, the episode added a wrinkle to his character, introducing his mysterious past as "Ripper."

Trick or treat

“Halloween” aired on Oct. 27, 1997, as the sixth episode of season 2. Written by Carl Ellsworth and directed by Bruce Seth Green, it’s the show’s first Halloween episode and its first holiday episode in general. It's also an important one for Buffy as a whole, coming in as the series was establishing its tone after a rocky first season. "Halloween" represented an upswing in its viewership, drawing almost 6 million viewers (a million more than the previous episode). It was also a rare instance of Buffy being rendered helpless, forcing the show's ensemble cast to rise up to the challenge, establishing some of the patterns they would follow in future seasons.

“Halloween” follows Ethan Rayne (Robin Sachs), a recurring villain from Giles' past, as he arrives in Sunnydale and opens a costume shop just in time for the holiday. He then calls on the two-faced god, Janus, cursing anyone who buys an outfit to become that character on Halloween night.

Buffy (Sarah Michelle Gellar) is late for a date with Angel (David Boreanaz), and spirals about their relationship, worrying he’d prefer to date a noblewoman from his past. Xander (Nicholas Brendon) is humiliated after Buffy defends him from a bully and wants to seem more manly. Willow (Alyson Hannigan) is struggling to step out of her shell, with Buffy encouraging her to wear a miniskirt and a tight top for Halloween.

The group buys costumes that match their insecurities, with Willow throwing a ghost sheet over her risqué outfit at the last minute. Come nightfall, the characters become their costumes: Buffy is a fearful 18th-century noblewoman, Xander is a tough soldier with a gun, and Willow is a ghost. With Buffy on the back burner, Willow and Giles step up: she shepherds the group to safety and leads him into Ethan’s costume shop. There, Giles reveals that he and Ethan share a past. He sends Willow away and beats up his old friend.

Ethan calls Giles by his old nickname, Ripper, introducing a background we never imagined to the show’s nerdy librarian and one of its rare steady adults. Giles ultimately saves the day, smashing the statue that powers the curse.

Meet Ripper

“Halloween” introduces a side of Giles that shows just what he’s capable of, and that complicates his character for the audience. Two episodes later, in “The Dark Age,” we get more of Giles’ past, revealing he and his old friends meddled with dark magic when they were young. The consequences of his actions come back to haunt his present and the things he cares about the most (a season later, the episode "Band Candy" would explore this side of Giles even further, but that's a story for another article).

Ripper remains one of Buffy’s most thought-provoking mysteries. It’s a side of Giles that he despises and hides. Still, he can’t fully escape from it. When Giles is cornered and at his weakest, his dark side emerges, resulting in some of the show’s most shocking turns.

In another world, we might have gotten a lot more of "Ripper." For years, Head and Joss Whedon, Buffy’s problematic creator and showrunner, discussed making a separate show called Ripper, one that explored Giles’ character after the end of Buffy. We’ll never know what the future holds for him and the rest of Scooby Gang, but maybe, in this era of zombie IP, that’s a good thing. However, in a 2009 interview, Head offered a hint at the meaning behind his character's nickname, and the themes the spin-off series might have explored.

"I don’t think we’ll ever really know [what Ripper means],” said Head back in 2009. “I think Ripper just means it’s the darker side of someone… that you never ever knew existed.”