Lyric discussion by LittleGreen5 

Cover art for Reason Why lyrics by Rachael Yamagata

I agree with most of the things people have said but I think this song is about Rachael's ex-boyfriend James. They were in a band together in Chicago called Bumpus but Rachael ended up leaving because she was under-appreciated and she wanted to try some songs that were very different from the material the band usually played. From my understanding, they made fun of her for it. They didn't like her "sentimental" music and wanted her to keep doing their kind of music. Anyway, she and James broke up and Rachael went solo.

So in reference to the song, they used to travel on the road while touring and could have continued to do so if they had stayed together. After breaking up, she used to look for him in magazines and would listen to them on the radio. Now James is the the lead singer (they used to sing together) so he'll steal the show and try to go back and cover the song tracks that featured Rachael. If either of them made it big, they could talk about their failed romance fondly.

So while the song can be interpreted many different ways because Rachael made it open ended and threw in a lot of double meanings, this song to me is ultimately about the demise of her relationship with James.