If you are like me, there are albums or songs that you listen to when you want to turn up the volume and sing along because life is good. Then there are songs that you crank up and listen to because they help you to feel the pain that you are trying to find a way to let out. And then, there is, at least in my experience, the hardest to find variety… the music that you listen to because it is actually a conversation. The lyrics resonate with you in many ways, challenge you in others, and help you think through the same old ideas in new ways.

In some ways Derek Webb’s music has played all of those roles in my life. Center Aisle and Table for Two from his Caedmon’s Call days helped me to wrestle with the loneliness that I occasionally wrestled with in college. I have also been known to just turn up the volume and sing along to Daring Daylight Escape and Thankful (also from Caedmon’s days).

But then in seminary I went to a concert to hear Caedmon’s Call. I was honestly going to hear Derek Webb sing the songs that were almost all of my favorite songs by Caedmon’s. Except he wasn’t there. After the concert I learned that he had left Caedmon’s to start a solo career.

And then came album after album that have brought both good music, and challenging, edifying lyrics. Each album has had different themes, but they have all had songs on them that were profound. “Crooked Deep Down” was my favorite on his first solo album, “She Must and Shall Go Free”. He sings:

my life looks good i do confess, you can ask anyone
just don’t ask my real good friends
because they will lie to you
or worse, they’ll tell the truth

because there are things you would not believe
that travel into my mind
i swear i try and capture them
but always set ‘em free
it seems bad things comfort me

chorus: good lord, I am crooked deep down,
everyone is crooked deep down.

and then there are the occasional lyrics that are just awesome, like at the end of “Crooked Deep Down” when he admits to having one thing on his mind, “squeezing me and my camel through the needles eye.”

And then there are the lyrics that just make you stop and think, because they are so powerful and so confrontational. A great example is from “My Enemies Are Men Like Me” from the album “Mockingbird”:

peace by way of war is like purity by way of fornication
it’s like telling someone murder is wrong
and then showing them by way of execution

He is one of the few people who I do not know who has helped me to grow in my faith. I am grateful for his music and his ministry. If you have not heard the music of Caedmon’s Call or Derek Webb, I would recommend them both to you. You can see the full listing of Derek Webb’s albums here.