His most recent album, "Stranger to Stranger," debuted at No. 3 on the Billboard 200 earlier this month, the highest debut of any solo album of his career. But, Simon tells The New York Times, he may be "coming towards the end."
"Showbiz doesn't hold any interest for me," Simon said. "None."
Simon is gearing up for the final shows of his current North American tour in Queens, New York, this week, where his career with Simon & Garfunkel began.
"It's an act of courage to let go," Simon said. "I am going to see what happens if I let go. Then I'm going to see, who am I? Or am I just this person that was defined by what I did?"
Simon explained that he struggles to write songs but suddenly finds himself thunderstruck by breakthroughs.
"I was 21, maybe 22, when I wrote 'The Sound of Silence,' which seems to me like quite a big jump from where I was before that," he noted. "I thought the same thing when I wrote 'Bridge over Troubled Water' -- whoa, that song is better than what I've been doing."
But he said the moments like that don't happen very often.
So will he actually retire after his European tour this fall? He's not saying definitively yes or no, but, he told The Times, "I don't have any fear of it."