He found the observation both useful and amusing. He has referenced it repeatedly in subsequent interviews as a kind of guiding principle for how to hold the whole experience: not personally, not possessively, not with either the grandiosity that would claim it as a triumph or the injured feeling that would experience it as an indignity.
The video from 1987 — directed by Simon West, filmed in a day across several West London locations, featuring Astley in what he has himself described as some of the cheesiest styling of the 1980s — was not something he made with any expectation that it would still be in circulation twenty years later. It was a promotional vehicle for a debut single. The moves, the clothes, the hair, the setting — all of it was the visual vocabulary of its specific moment. Astley has said, directly, that he finds most 1980s videos pretty cheesy. He is not wrong. The video is very much of its moment. That quality — its specific, emphatic, unavoidable 1987-ness — is part of what makes it such an effective carrier of the joke.
## The Mechanics of the Prank
Understanding why rickrolling worked as a meme requires understanding the specific conditions of internet use in 2007 and 2008, which were different from both the early internet and the contemporary internet in ways that made certain kinds of pranks particularly effective.
In 2007, link previews — the technology that shows you a thumbnail and description of a link’s destination before you click — were not universally implemented. Shortened URLs, which disguised the actual destination of a link, were widely used. Forums and comment sections on websites regularly hosted hyperlinked text with no indication of where the link actually went. The text that appeared as the link was frequently misleading, and the only way to know where a link went was to click it.