Yusuf told The Sun May 1, 2009 that this song is, "a story of prejudice and there's a lot of that that around!" He added: "We have to deal with it and one way is symbolise the character, you know the outcast as a Roadsinger. He's a busker in a way. He's well traveled."
Roadsinger was the former Cat Stevens' follow-up to his 2006 set An Other Cup, which was the Muslim singer-songwriter first secular album in 28 years. Yusuf told Billboard magazine: "This one was really a result of me writing a lot of songs and being kind of inspired again. After I recorded ['Cup'] people just wanted to hear me do a lot of simple stuff, just with the guitar."
Mojo magazine June 2009 asked Yusuf if this is an autobiographical song. He replied: "It is but these days it's with a small 'i.' Would it have been with a capital 'R' before? Yes. But these days I can see myself drifting in and out without any problem. I'm just leaving a little trail, a little message about where this road singer's been. Somebody may pick up on that, may understand it, may want to know more, or may just move on. The road singer's there if you want to him. He's around."