(Credits: Far Out / George Michael)
Mon 11 August 2025 15:30, UK
As one of the UK’s greatest exports in popular music, you’d think that George Michael wouldn’t have had too many regrets in his life, having lived a bountiful and celebrated existence up until his untimely passing in 2016. With a career that spanned across four decades and saw him reach number one in the UK charts a total of 11 times during his lifetime across all of his different projects, there’s arguably little that could have been keeping Michael up at night with regards to his achievements.
His spell as one half of the pop duo, Wham!, was what propelled him into the spotlight in the first place, and alongside Andrew Ridgeley, he managed to establish a stranglehold on the pop sphere through the release of beloved tracks such as ‘Wake Me Up Before You Go-Go’, ‘Freedom’ and ‘Everything She Wants’. It was unusual to see a British duo of this ilk managed to successfully crack America during this period, yet their second album, Make It Big, managed to go to the top of the charts on both sides of the Atlantic, rendering them global superstars.
However, the short-lived nature of Wham!, which saw Michael and Ridgeley go their separate ways after just three records and five years together, meant that Michael had to then establish himself as a solo artist. With more than enough talent to show, he was able to not only continue in the same vein as he had in his band, but would go on to have an even more illustrious solo career, continuing to reach the top of the charts throughout the late ‘80s and ‘90s.
During this solo career, Michael collaborated with a number of other big names in pop, releasing songs alongside Elton John and Aretha Franklin that topped the charts. It’s hard to think of anything that George Michael did artistically and declare it a failure of any kind, so what could he have possibly held any regrets about?
In a 2014 interview with Mojo, he was asked to deliver a ‘self-portrait’ of his life and career, answering some of the deepest questions about his trajectory, and this is where fans would finally discover what his greatest regret had always been. It may not have been anything to do with his releases that kept him awake at night, but more a case of him finding it impossible to get over having turned down a once-in-a-lifetime opportunity to perform with rock royalty.
Despite joking to the magazine initially, telling them “my biggest regret is splitting Wham!”, he would go on to reveal that something else has always haunted him to a far greater extent. “On a serious note, there are probably so many,” he continued. “I think I’ve mentioned it before, but not performing with Dave Gilmour at Carnegie Hall. That one slipped under the radar!”
This might not be what fans of Michael would expect him to come out with as a response to this question, but in all honesty, he was hardly going to have any complaints about his own career output, given how successful it was. If you’re given a chance to play with someone as legendary as the Pink Floyd guitarist, you’ve kind of got to take it, and that makes it all the more understandable that Michael would regret this missed opportunity.
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