‘Brown Sugar’ – The Rolling Stones

Since their formation in 1961, The Rolling Stones have made some…questionable decisions.

From their rise to the top as one of the most raucous and rowdy rock ‘n’ roll outfits in the rock scene to their more recent dabbles in the world of deepfakes and AI, suffice it to say that Mick and Keef are quite possibly one of the messiest musical duos of all time.

However, one of their worst decisions no doubt has to be ‘Brown Sugar’, a song so problematic and degrading that it’s actually impressive. While some claim its meaning leans more towards a term for heroine than anything potentially sexist or racist, there’s no denying that it was intended a certain way, a fact the band themselves acknowledged when it was officially dropped from setlists in 2021.

‘Imagine’ – John Lennon

Hear me out. Obviously, John Lennon’s ‘Imagine’ is one of the most iconic songs in history, and one that quite clearly altered the landscape of music in ways we’ll never truly understand. But it also stands as a glaring representation of everything bad about tired old hippie idealism and cultural pretentiousness in 2026.

To prove this point are two obvious examples of recent pop culture offences: Millie Bobby Brown’s infamous singing meme, which stemmed from a livestream when she was around 12 years old, and Gal Gadot’s horrendous 2020 lockdown video campaign that she organised to raise morale during the Covid-19 pandemic.

Granted, one is harmless, and the other is, well, a modern-day manifestation of peak celebrity social cluelessness, but both are evidence that ‘Imagine’ has become the ultimate symbol of modern-day performativity and social media brain-rot.

‘Bip Bop’ – Paul McCartney

It’s very rare for Paul McCartney to be negative about anything, especially now, when looking back at everything he achieved in the 1960s and 1970s. However, there are some decisions that he just can’t look past. ‘Bip Bop’, for instance, from Macca’s debut album with Wings, Wild Life, is one he’d have understandably rather left in drafts.

In fact, the former Beatle felt that the song was so bad that he told Q Magazine, “The lyrics are fucking awful”, addressing the strange scat-singing and nonsensical words and phrases towards the end of the track. Not McCartney’s finest hour, but if for nothing else, suppose it does showcase just how much he was willing to test the waters at the start of his own career.

‘Gypsys, Tramps & Thieves’ – Cher

Cher might not rank that highly when it comes to problematic legends, but a couple of her songs are a little questionable, much like the Stones’ stint with ‘Brown Sugar’ (and the countless other sexist songs they somehow got away with all those moons ago).

‘Gypsys, Tramps & Thieves’, as the title overtly suggests, is one of those songs that probably should never have made it out of the recording studio. Once deemed as one of the best singles of the entire decade, the song is no doubt one of the catchiest in her discography, though it’s also pretty offensive looking back now, especially when it comes to the derogatory slur in the title and the implications that come with it.

‘One Bad Apple’ – The Osmonds

Originally written by George Jackson with the Jackson 5 in mind, ‘One Bad Apple’ tells the story of a boy convincing a girl that he deserves a chance and that “one bad apple” shouldn’t inform her future decisions in life and love. Similar to another Jackson 5 hit, ‘I Want You Back’, ‘One Bad Apple’ is exactly the kind of song you’d expect to become a hit in 1971, capitalising on that familiar R&B pop sound that became a dominant force in the early ‘70s.

However, all things considered, it’s hard to ignore what ‘One Bad Apple’ actually was, aside from its obviousness as a poor white imitation of the real thing. It was also the epitome of stealing ideas for the purpose of commercial pandering, lacking any of the original authenticity of the styles it attempted to emulate and ultimately lacking any sort of character or depth.