(Credits: Far Out / Recording Academy)
Mon 24 November 2025 6:00, UK
Winning a Grammy is, to most people, the pinnacle of success. You can’t possibly get any better than that. Right?
Technically, that only rings true depending on what an artist categorises as “success”. For some artists, being successful means having full creative control and making their own decisions, both in the writing process and in the studio. For others, that’s only a part of the full picture, and the rest comes with earning a satisfying amount of recognition after the fact.
Historically, countless artists have struggled with the implications of mainstream success and what awards like the Grammys actually mean. Of course, at the crux of it, it’s about celebrating and honouring art that has a profound impact on audiences and culture. But beyond that, it’s sometimes seen as another empty emblem of accreditation for something that may or may not be considered worthwhile when it comes to artistic expression.
Obviously, all of that comes with the caveat that all art is subjective, and someone like Bruno Mars winning a Grammy might seem like a cause for celebration to some but a nightmare to others. At the same time, the Grammys aren’t exactly a stranger to such controversies and often thrives on it, too.
In fact, some of the most polarising moments in music history have come from the coveted awards ceremony, but this proves how relevant they still are to the modern music community and, perhaps more importantly, how much the organisers use audience reaction as a soundboard for ensuring their own processes and approaches are up to standard.
Who was the first person to win a Grammy as a solo artist, duo, and part of a group?
A good example of this is when the R&B duo Milli Vanilli had their Grammy revoked after winning Best New Artist in the 1990s. The reasons why were simple – they weren’t using their own vocals when singing their songs – but more than that, it sparked a turn in the organisers’ strategy that meant they were far more stringent when it came to nominees and far less embracing of acts they didn’t consider wholly worthy of such a recognition.
But the Grammys aren’t just about controversies, though those moments have provided some of the more interesting aspects over the years. In fact, the Grammys have been at the forefront of musical excellence for decades, celebrating timeless legacy acts, from Stevie Wonder to Paul Simon. Simon, in particular, is a unique case in that he holds the position as the first to win as a solo artist, duo, and as part of a group.
In 1969 and 1971, Simon won as part of Simon & Garfunkel for ‘Mrs Robinson’, and in 1986, he won as part of the USA for Africa group for ‘We Are the World’. He then won as a solo artist in 1988 for Graceland, a special recognition as Album of the Year for Simon’s labour of love that saw him going against advice from all corners of the industry to realise his artistic vision.
Political context aside, it was the record that solidified Simon’s place in music and Grammy history, on account of his mastery of mixing traditional South African sounds with his familiar folkish flavouring. It might have seemed a major risk at the time, but one that was ultimately worth it to make its way onto countless lists accumulating the greatest records of all time.
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