Until recently, I've fallen into the trap of overlooking large chunks of Bob Schneider’s career. As a music fan, I hope this is understandable, if not forgivable. After all, the prolific Austin-based singer/songwriter/multi-instrumentalist's discography recalls one of my dad’s favorite maxims, "There's nothing constant but change." It's very hard to catch up.

But also very rewarding.

For two decades, Schneider's musical verve has run a gamut of styles, heavy on both variety and passion. At some point in your listening career, you may have encountered an incarnation of his music. The man works hard at what he does, and he sells it well.

Perhaps you caught a set full of homegrown tunes from his former band, The Ugly Americans, billed with Blues Traveler and The Black Crowes on 1994's H.O.R.D.E. Festival Tour. Or maybe you heard his spirited solo performance, "Bullets" from the acclaimed soundtrack to the Kevin Smith film Jay and Silent Bob Strike Back, and bought his lauded 2001 album, Lonelyland.

Or possibly, like me, you might have caught a funky set from him when he and The Scabs played downtown at the now defunct Engine Room back in 2002.

Whatever the context, it's likely that Friday night's performance at the Wortham Theater Center's Cullen Theater, billed as "A Holiday Eve with The Moonlight Orchestra," will yet again be new territory for Schneider fans and newcomers alike.

CultureMap: How did you come to play with the Tosca String Quartet?

Bob Schneider: I recorded a little bit with them back in 2006, and I've played on and off with them ever since.

My newest record contains arrangements that I wrote for them, so last Valentine's Day I thought we'd try a show together in Austin. That show was a huge success, so I wanted to take it to Houston and Dallas this season. I never do anything like that here.

CM: I caught a YouTube performance from that Valentine's Day show and it struck me that so much of your music is very adaptable and diverse. Is this orchestra tour something that you’ve always wanted to do?

BS: Anything that I've ever done just sort of happens. I didn't have a master plan to do something like this, it just kind of occurred. I've learned that I love playing with a jazz orchestra. You can do a lot of stuff that's pretty fun with that kind of setup; strings, piano, instrumentation like that. It allows a musician to set the scene emotionally in a way that's pretty powerful. Dramatic results happen.

CM: Has it been difficult to adapt your catalog to this context?

BS: Some songs of mine, like [2007's] "Changing Your Mind,” don't necessarily work with the strings, so we stick to what does work. You might hear a great version of "Honeypot" on Friday, for example.

Ultimately, our goal is to make the show interesting and have it not be redundant or monotone. No matter how good a show is to me, I get bored if the music is the same throughout the set. So we are going to make this more than just an evening of jazz standards.

You'll hear songs with just [Austin songwriter] Lex Land singing, you'll hear traditional jazz covers and you'll hear a few songs of mine that you're used to. We won't do cheesy holiday stuff like "Jingle Bells" for this show, but I can promise that we're going to have a lot of fun at Cullen Theater.

CM: What sort of advantages does playing in a theater afford a musician?

BS: There's the obvious sound quality factor, definitely. It's also great for the listener because you can sit down and enjoy the show without having to strain over the din of drunk people talking or have to endure being jostled in a crowd for the duration of the show.

It's great for me too. I'm not having to compete with people talking with each other, and it makes it way more enjoyable. That audience intimacy lets me know that they are being heard and that makes me want to do my absolute best to deliver a great show.

CM: Do you intend to explore this (Moonlight Orchestra) pairing more in your career, or is this tour designed to be an annual holiday treat?

BS: At this point, it would be hard to take it outside of Texas. I would love to do this nationally, but it's very difficult at this point. It’s a big undertaking to ask that many musicians to travel, and there is a lot of stage set-up involved. Until I get a bigger audience nationally, it would be hard to do this with any regularity.

CM: What advice can you give fans that might be be more accustomed to your traditional set lists?

BS: There are two people that come to my shows, and both types will have a great time. I think that people that may have just heard a couple of songs by me will be pleasantly surprised by [the] show, because it's going to feature such a broad range of music. I think people will enhance their enjoyment.

On the other hand, I feel like the people that have followed what I have done for the last few years know not to expect anything but spontaneity. We're all over the place, stylistically, so those that have been to a lot of my shows expect nothing more than a certain level of quality. They know they will have a good time and will be entertained.

Bob Schneider and the Moonlight Orchestra perform Friday at Cullen Theater. Click here for more details.