There are very few constants over the last 20 years of my life. One of them is the friendship of my good buddy, Ryan. Another is the work of singer/songwriter/entrepreneur derek webb. (He doesn’t capitalize his own name, so why should I?)

If you’ve been around TWS for any length of time, you’ve probably seen me drop derek’s name. I had the chance to see him in concert last Friday, but first some backstory.

I have an absolutely clear picture in my mind of the first time I heard a derek webb song – “Not the Land” from the self-titled Caedmon’s Call record (1997). It’s not a nostalgic thing at all. It was as though I knew in that moment that a switch had flipped for me somehow. His was the music that prompted me to begin songwriting.

Ryan and I saw our first Caedmon’s Call shows together in 1998 and 1999 before separating for college. I caught another show my freshman year and then worked as a promoter for two shows during my senior year. During that time, derek launched his solo career – another tour I had the opportunity to work on. Flash forward and I caught another show in the early 2000s, then Ryan and I re-grouped for a show a two years ago (pictured above). I was debating going to go to last week’s show when Ryan called and told me he had bought us tickets and wanted me to go with him. Man, am I glad I did.

I’ve seen shows from derek (and his former band) in churches, colleges, bars, and weird multi-use spaces. This one was particularly cool as it was an old community theater which had been bought out by a small progressive church. We sat on the front row with our fee up on the stage. The last show we went to was just on a flat floor with a bunch of folks crowded around. derek sat on a stool. This time he stood and the elevated stage and lighting created a buffer that I imagine was probably needed for everyone’s good as our old friend somewhat reintroduced himself as an artist.

I won’t seek to explain or label derek’s spiritual history but I’ll try to put it like this. His first solo record (She Must and Shall Go Free) was firmly and explicitly about the Church. His last record (I Was Wrong, I’m Sorry, and I Love You) was very strongly about the Church. And along the way he has explored topics of justice (Mockingbird), politics (The Ringing Bell), technology (CTRL) and more. While he has often challenged convention, his music has always kept a very strong tie to the Christian faith.

The last time we saw him, he was newly divorced – a topic that was not explicitly discussed during the show. There was no new content and songs about his ex-wife were preempted with some discussion of being a documentarian and having documented his life and then making his living by singing about it. He talked about finding new ways to connect to old songs and maintaining a connection the work of the man he previously was.

Saturday’s show began with a few older songs – including a personal favorite, “I Want a Broken Heart” – before revisiting the preemptive diatribe with greater fervor. webb fashioned himself as a man who consistently finds himself performing another man’s material. That is, he is no longer the man today that he was when the songs were written. He says that this even applies to his newest work. This, of course, absolves him of any need to believe the same things in the same way that he once did. Thus, the content was really varied.

That said, it was notable that he kept his older material mostly focused on themes of social justice. This meant performing material from his Mockingbird and The Ringing Bell records. He did manage to slip in the Stockholm Syndrome track “Freddie Please” which I had never realized bears a striking resemblance to “Earth Angel.” (Relevant as webb has always been a fan of Back to the Future).

But the big item on the agenda was webb’s new material. Tweets have teased derek’s recent work over the past few months including a self-proclaimed “worship song.” At the same time, a rather large number of tweets have referenced extensive time spent at the local bar – a theme that is strikingly present in the new material.

In all, 5 new songs were played including the previously released single “The Braver One.” I hesitate to reveal too much as the experience of hearing these songs for the first time nearly sucked the air out of the room. At times, post-song applause was withheld a split-second longer than expected; long enough to cause worry.

After the show, I commented that this was the most honest and authentic work I had heard from him in 20 years. He dealt very directly with issues of family and divorce (a theme explored even more on his forthcoming record in a song not played at show). He spoke honestly on matters of faith and God.

derek clearly knows that these new songs put him at risk of losing fans. I assured him, however, that I know plenty of people who have been fighting to find words for their journey who will be so grateful for these songs. In fact, one song in particular echoed a sentiment I’ve heard numerous times,

So either you are not real

Or I am just not chosen

Maybe I’ll never know

Either way my heart is broken

If I could, I’d follow this guy around every night to hear these songs again and again. A date has not been set other than “Fall” for the new record. Fortunately, derek will be on tour throughout the U.S. this summer. Try to catch him if you can. Tour Dates Here.