Ylove and Dov both offered some of their favorite examples, Ylove presenting "Forest" and "Question" from the band System of a Down and Dov presenting Spiralling by the band Keane. Neither bands are Jewish, none of the three songs were written from a Jewish perspective, but each song strongly resonated for one of the presenters and was analyzed for it's spiritual content. For example "Forest," to Ylove, was a retelling of Genesis that emphasized the balance of Yetzer Hara (the evil inclination) and Yetzer Hatov (the good inclination) and was suggestive of the Midrash that described Adam as temporarily becoming an atheist and denying the existence of God.
Walk with me my little child
To the forest of denial
Speak with me my only mind
Walk with me until the time
Make the forest turn to wine
You take the legend for a fall
You saw the product
Why can't you see that you are my child
Why don't you know that you are my mind
Tell everyone in the world that I'm you
Take this promise to the end of you
Honestly, I struggled with this conversation. Alan, Dov, and Ylove are all Orthodox Jews and this kind of handwringing justification for secular music is a preoccupation of folks from the traditional Jewish community. Those of us in the liberal community don't have any religious obstacles to overcome regarding secular music and don't feel the need to justify listening to it. Because of that, applying derash techniques to extract moral or theological lessons from secular pop songs seems both unnecessary and misleading. Ylove noted more than once that the spirituality of a song is very much up to the ear of the listener. I worry that a better analogy is that the listener is mining for gold with a paint brush and gold paint. Anything of value that was found was placed there by the searcher.
On the other hand, I found the conversation strangely liberating. Over the years, while I have fought off the constant bombardment of Christian lyics, I have run into a number of songs that have affected me deeply in a very positive, very Jewish way. I often struggle to say why, though. For example, I have been deeply moved by The Waterboys and XTC's British pagan pop songs. While the literal meanings of the songs go against my beliefs, there is something about the unapologetic sense of awe in an imminent God in them that I resonate with. To Ylove and Dov, that's a good thing. To them I'm capable of extracting the spiritual value of the song and letting the other bits go. The fact that I'm training my ear to hear the songs Jewishly is the important thing.