A sophomore effort, I See Things Upside Down, followed in 2004, along with a live album, The House Show.

His 2005 release Mockingbird earned rave reviews and elicited responses ranging from deep appreciation to bristling concern due to its controversial subject matter.

Then in late 2006 he poured fuel on the fire by giving away over 80,000 free downloads of the album on-line in partnership with his label INO Records. Major music industry media wrote all about the radical idea, and the nouveaux troubadour saw his concert audiences double in several markets.

By daring to tackle difficult subjects like ethics, politics, and personal integrity with disarming vulnerability, Webb turned more than a few heads in the music industry.  He released a concert DVD How to Kill and Be Killed that same year.

Derek's latest release, The Ringing Bell (2007).

As the title suggests, this collection sounds clearly through the noise of the day, beckoning some, and warning others. It’s a call to meaningful conversations and it’s a great time. It injects songs into the cultural bloodstream that will move listeners to reflection and action while moving their feet. For, while those who have followed Webb’s career, first as a member of Caedmon’s Call and then as a solo artist, will not be surprised at yet another collection of memorable, reflective and significant songs, they may be surprised to hear the Texas native rock and roll.

In this album he explores the idea of Peace. 

“I don’t do things in moderation,” Webb admits enthusiastically, “so when I get into an idea or concept I really get into it. When I study a certain thing I will pile up books about that subject and just go crazy for awhile learning it.” On the heels of Mockingbird, and following numerous confrontational and challenging conversations with fans on the road, the difficult subject was close to his heart. “I think The Ringing Bell is a record about peace on the whole,” he explains. “Several of the songs have to do with peace, be it literally or conceptually or personally or nationally or even spiritually.” In fact, the title of the album’s thesis track, “A Love That’s Stronger Than Our Fears,” is cribbed from the subtitle of John D. Roth’s influential book Choosing Against War, a recent favorite of Webb’s.

“I felt like there was more to say about the subject,” he says. “I wanted to get further into the nuances of it. This is too important of a moment historically to not say more about the idea of peace. It’s right in my face at all times if I claim to be at all concerned with anything that Jesus ever said.” Not that he considers himself an expert or perfect practitioner of the concepts he is exploring. In fact, it is his own personal struggle with being a peaceable person that fuels his songs. “I feel like I have violence in me,” he admits, “that if left unchecked, could show itself in really ugly ways. It’s not just physical violence, but emotional and relational violence. John Lennon was asked about the peace movement he was a part of in the 1970s and he said ‘I don’t do this because I’m peaceful. I’m a really violent person.’ That’s probably why I’m so drawn to this. I know what an important issue this is because it’s an issue for me. I don’t know much about peace; it doesn’t come naturally to me. I don’t like it. It’s not ‘natural.’ It’s counterintuitive.”

Webb’s charm and humor is a major ingredient in the album’s effectiveness. Songs like “I Wanna Marry You All Over Again,” and “Name” bring a light and even playfully romantic quality to the collection, while “A Savior on Capitol Hill” rocks hard and lands its jabs with a wink. “In Caedmon’s Call,” Webb reflects, “it fell to me more to write the more light-hearted and relationship oriented songs. This record definitely has some humor to it, as well some real serious rock and roll moments, which hasn’t happened for a while.”

“I hope that this record is a bit of a surprise,” he adds. “Inadvertently I feel like I have somehow mysteriously made my most commercial record,” he laughs. “It’s definitely my most accessible one. I feel like it brings together the best elements of what people have liked about my music up to this point.”