“Rehab,” the leading single off of Back To Black, arguably put Winehouse on the international map. The song is a hauntingly ironic, upbeat tune where Winehouse refuses to go to a rehabilitation centre to help manage her drug and alcohol problem.

Despite her resistance against any form of professional rehabilitation, she ended up checking into a rehab centre in early 2008, leaving just in time for the 50th Grammy Awards where she would take home a Grammy for Song Of The Year, Female Pop Vocal Performance, and Record Of The Year, each for “Rehab.”

While the song brought her much success, its message was questioned by listeners who were concerned for Winehouse’s health and addiction problems in real life. Almost four years after her tragic death, Winehouse’s former manager sat down with The Guardian in June 2015 and revealed how “Rehab,” specifically, had left a mark on him and those close to Winehouse, saying:

I knew at some point she’d write a really big hit, and it was ironic that the hit she wrote was, verbatim, that day, and it was mocking me. Not only was I not her manager any more, but she’d written this huge hit that’s undeniably brilliant, that was a complete mockery of our friendship and of what she needed. And the whole world’s dancing along to it, and really she was writing about a decision that five years later would result in her being dead. It was really fucked up. […] I can’t really listen to Amy any more, unfortunately. If I walk into a shop and she’s playing, I always get a little sense of pride and warmth, but I can’t put it on.