Before Google, there was Ask Jeeves, a website where curious internet users could put their queries to a cartoon valet. The valet, like the PG Wodehouse character that inspired his creation, was pinstriped, serene, and polite, if not quite as effective. Jeeves was eventually outmoded by Google, but his website, shorn of its mascot, persisted in the form of Ask.com.

Now, almost 30 years after Ask Jeeves was founded, Ask.com has itself been shuttered. Were it not for nostalgic recollections of Jeeves, the shuttering would have passed almost unnoticed; instead, many have written fondly of the cartoon valet and of the simpler era of internet history that he now represents.

As some have already noted, Jeeves is a better fit for today’s large language models, which are knowledgeable and articulate, than for the rudimentary search technology of which he was a figurehead. Yet it is hard to imagine an English valet becoming the face of ChatGPT, Gemini or Claude.

That is partly because cartoon avatars, as demonstrated by Microsoft’s word-processing assistant, Clippy, have fallen out of fashion. But even if cartoon avatars were to come back into vogue in tech, they would be unlikely to take the form of understated English valets. Ours is a different world from that of 1996, when Ask Jeeves was conceptualized in Berkeley, California. Wodehouse himself, who had died in 1975 in the Hamptons, was still a recent memory; perhaps a few paperbacks of his could be found in the parental homes of Ask Jeeves’ creators. The Fry and Laurie adaptation was even more recent a memory, broadcast in Britain from 1990 to 1993.

Crucially for Ask Jeeves, a much higher proportion of internet users were in Anglophone countries than is the case today. Most users of the service would have been American, and America itself, with several decades of falling birth rates and rising immigration yet to come, had proportionally more diaspora Britons among its population than it does in 2026. As the composition of a market changes, so do its cultural referents.

Britain itself still had a parliamentary chamber full of hereditary peers: precisely the kind of person whom a fictional valet would serve. Most of those peers were soon to be swept away by a Blairite government for whom egalitarianism was a lodestar. A valet connotes precisely the kind of rigid class system that Blair, in common with progressive politicians elsewhere, was seeking to dissolve.

If deployed today, then, a digital valet might be off-putting to progressive Westerners, who are uncomfortable with traditional social hierarchy. As for non-Westerners, who now form the majority of Internet users, they would simply be nonplussed. Where Nineties software was sometimes playfully non-optimized, today’s mass-market LLMs require as close to zero cultural context to operate as possible.

Jeeves, then, is unlikely to return soon to such a prominent place in the American imagination, and in this respect, he is a parable for his homeland. In 1996, Britain’s GDP was bigger than China’s and India’s put together. Its governance was widely respected. Blair, when he arrived in Downing Street the following year, could position the country as America’s Middle East aide-de-camp, its Brussels concierge — and perhaps, in some ways, its valet.

Yet in military terms, Britain is now unable to play even the second fiddle. The transatlantic relationship has been strained emotionally, too. To misquote Dean Acheson, the gentleman’s gentleman has lost a job and not yet found a role.