He was taking part in Vendor Week to help raise the plight of the homeless in his home city.
And he admitted his lead singer ego took a bashing when some people ignored him, but it gave him a real insight into the lives of the homeless.
Many people did recognised on e of Sheffield's most famous sons and one even asked if he had fallen on hard times, he laughed.
But he hopes giving time to highlight the cause and the good the Big Issue does, helping homeless people to earn and turn their lives around, will encourage more people to stop nd buy a copy.
Jon has also encourage Big Issue charity collections at his gigs and says he will continue to back worthy causes.
In an exclusive chat with Digital Editor Graham Walker - click here to here th interview in full - he said: "It's a nice thing to do, to put a bit back.
"I've just wanted to do my bit as part of Vendor Week, which is about getting people like me to sell the Big Issue. Homelessness shouldn't really be a thing these days.
"When you walk in town and see homeless people it goes through me.
"The Big Issue enables people to do earn a bit of money.
"I was told today about a man who used to sell the Big Issue outside a cafe in town and he's sorted himself, got a place to live and through selling the Big Issue he's got a job inside the cafe where he use to sell outside. Just a fantastic story.
"I'm the lead singer in a band and I'm used to people cheering and going mad, when we go on stage. Today I was offering people the Big Issue and they were ignoring me and walking past. It's a bit of a blow to the ego as a lead singer to be ignored.
"It was an insightful moment.
"A few walking past did recognise me. One asked if I had fallen on hard times. Sheffield is a very friendly city and I think people were pleasantly surprised to see me out there. Hopefully it put a smile on people's faces.
"I did it for an hour and it was howling down, wind, cold and I was freezing by the end, drenched and I thought, imagine having to do this all day. So it's to raise a bit of awareness."