(Credits: Far Out / Album Cover)
Sat 6 December 2025 4:00, UK
Paul Simon hasn’t become one of the greatest songwriters of his generation without making a good share of mistakes along the way.
As long as Simon and Garfunkel were together, there was always that little bit of tension that ate away at them, and even though Simon went on to a stellar solo career, there were bound to be a few times when he felt he could have done something differently with his old friend. But he was also quick to see when some of the new kids on the block were going to be shaking their heads in later life.
Then again, it’s not like Simon has written the greatest songs on every single album he’s ever made. He is correct when he said that a track like ‘The Sound of Silence’ would be remembered for centuries to come, but it’s not like he’s exactly itching to play along to a song like ‘The 59th Street Bridge Song’ every time he performs. He was far more comfortable making songs that told stories in his later years, but the vernacular got a bit different along the way.
While Graceland showed that Simon could adapt to the times when he wanted to, the entire musical landscape was about to be changed around the same time. Around the time that a song like ‘You Can Call Me Al’ was one of the biggest tunes on MTV, there was also the beginning of genres like hip-hop, slowly beginning to trickle into the mainstream when bands like Run-DMC and Beastie Boys started blowing up.
It was a little bit alien for rock stars to see people using samplers on their records, but it’s not like rap and rock were all that different. Both genres were made for the disenfranchised, but if someone like Tupac Shakur or Biggie Smalls talked about how tough life could be on the streets, Eminem was one of the first people to take the darkest subject matter ever created and make it sound like some twisted version of a cartoon.
Dr Dre already had a history of working with the most dangerous men in the industry, but hearing Eminem’s music was uncomfortable even for people who listened to nothing but metal during that time. He wasn’t exactly telling people to kill their parents, but hearing his personal exploits was always going to be a little bit uncomfortable, whether that was his personal struggles with drugs, his strained relationship with his mother, or pretty much every single second of the song ‘Kim’.
While Eminem was certainly a wordsmith on par with the greatest lyricists of all time, Simon did think that he would live to regret all of the intense parts of his discography, saying, “At a certain point, you begin to realise about your life and your private affairs that it’s inappropriate that it should be entertainment for somebody else. There’s no requirement that I tell how I hurt and how I feel. It’s a mistake you make early on. I see Eminem out there talking about his family, his kids, and I think ten or 15 years from now he’ll regret it.”
But Eminem was never going to be dishonest in his music. Sure, some of those ugly chapters of his career are going to be there forever, but it was always about how he was feeling at the time as well. And looking at what he did on The Marshall Mathers LP 2, he did at least make peace with that side of his career, like when apologising to his mom on ‘Headlights’ or being able to walk away from his relationship with some grace on ‘Stronger Than I Was’.
Then again, the difference between Simon and Eminem comes more from the way that both of them write their music. Simon certainly is within his rights to air out the details of his private life if he wants to, but if he was able to weave together a character portrait around much of his heartache, ‘Slim Shady’ had no problem taking every detail and laying it out for the world to see.
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