André 3000 and the longest songs ever to make it into the Billboard Top 100

Taylor Swift - "All Too Well" - 2021. 10 minutes, 13 seconds

Not to add to the Taylor Swift canonisation, but the "Taylor's version" series of album rerecordings is probably the smartest, savviest move I've ever heard of in the music industry. With the rerecordings, she's turned an obscure convoluted music label stoush into a project that has energised her usually mellow fanbase and has guaranteed a string of number-one albums.

"All Too Well" was originally from her 2012 album Red; when Red was rerecorded in 2021, "All Too Well" was scaled up to just over ten minutes. That version was helpfully entitled "All Too Well (10 Minute Version) (Taylor's Version) (From the Vault)," which may well be the most parentheses ever on a song title.

But there is one record we do know "All Too Well" holds. It's the longest song ever to hit number one on the Billboard chart.

"All Too Well" is a power ballad and a story song, supposedly about her relationship with actor Jake Gyllenhaal. T-Swizzle doesn't get enough credit for her story-telling abilities. As if to prove herself in this arena, the video for "All Too Well" is a 15-minute short film that was released into cinemas, and is Swift's directorial debut. "All Too Well: The Short Film," and even generated Oscar buzz. In 2022, Searchlight Pictures announced that Swift had written an original screenplay, and would direct a feature film.