Al Howard likes to keep busy. The songwriter behind The Heavy Guilt and The Black Sands could easily fill his time with those two groups (not to mention writing for Owl and Bear), but he’s just added a third project to the mix.

That band, The Midnight Pine, centers around 21-year-old prodigy Shelbi Bennet, whose tender, ageless vocals recall everyone from Billie Holiday to Beach House’s Victoria Legrand. The Midnight Pine’s sound is steeped in the same time-tested, vintage songwriting that influences each of Howard’s bands, but it’s ingrained with a rustic, folksy feel that distinguishes it from its sister projects.

The Midnight Pine have already recorded their debut album, Awake Now, available now through iTunes. The band is playing the Tin Can Ale House on December 19 and will officially celebrate the album’s release on January 12 at Jett Gallery with fellow San Diegan folkster John Meeks.

We sat down with Howard to discuss The Midnight Pine, the band’s formation, what’s next for the talented songwriter, and why he doesn’t sing his sandwich orders.

Owl and Bear: You’ve chosen female singers for The Midnight Pine and The Black Sands, and you and guitarist Sean Martin are in both groups. In what ways are the two bands different?

Al Howard: The Black Sands was intentional — I was out actively looking for a female vocalist and Heather Marie answered a long-standing question with perfection — but The Midnight Pine was an accidental necessity. As soon as I heard Shelbi sing the immediate thought was “Ok, I know what I’ll be doing this next month.”

Like the Guilt and initially the Sands, most of [The Midnight Pine’s] music was written by Josh Rice (Heavy Guilt’s keyboardist), but Josh has a lovely 3-year-old to raise, so his participation has to be from a safe distance, not all papas can be rolling stones. Sean is the most incredible guitarist I have the pleasure of knowing; he’s versatile and has a great sense of tone and purpose, so I get him in on anything I’m doing. We work well together and he breathes to play music, so he makes it fit in his schedule.

The Sands have more rock in the arsenal; it’s a 7-piece band and drummer Jenny Merullo pushes us to have a nice dynamic between the delicate and the pummeling. [The Midnight Pine singer] Shelbi’s voice is so unique and haunting, I wanted the accompanying music to match her with a ghostly sparseness, to have no drums so the full attention was on the voice.

Owl and Bear: How did you discover singer Shelbi Bennet?

Al Howard: I met Shelbi at Cow — that’s the record store in OB where I’ve been working the past 5 years. She came in with three young brothers who I had been chatting up every Wednesday for a few years. The brothers would always astound me with their musical knowledge — I attribute it to the internet and them being awesome, but I can’t help but wonder how awesome I’d currently be if owned Television’s Marquee Moon before I was eligible to get a learner’s permit.

Anyway, one week she was there with them and after watching this Nina Simone video she told me she sings. I said I write songs and we should get together. Funny thing is I figured “I sing” meant “I sing in the shower and when I drive” and she probably thought “I’ll write you some songs” meant “I’m a creepy man 14 years older than you trying to do some dirt on the sly.” We got together once, she sang the song “Stolen Wind,” and I had a tear in my eye. It was the same feeling I had when I heard [the Heavy Guilt’s] Erik Canzona sing “Clove.”

Two weeks later we had about 13 songs and were figuring out what possessions I’d have to sell to make a record. The thing to keep in mind is Shelbi is 21 years old — the only reason anyone would be interviewing me at 21 is if a crime had been committed. It’s taken me 34 years to learn how to record an album like this and this is her first record. My inner hippie feels so blessed to play a part in this young talent’s career, to know the confidence she wields and the humbleness which keeps her grounded. My inner Jersey asshole hates her for being young and knowing what the fuck she’s doing.

Owl and Bear: Which bands do you think most actively inform The Midnight Pine’s sound?

Al Howard: Mazzy Star and Karen Dalton was what I heard as a goal, and Karen sounds like Billie Holiday singing Dylan songs. I’d say lyrically Townes Van Zandt, Leonard Cohen, and Bob Dylan. Sonically Nick Drake, Wilco, Jason Collett, Mark Lanegan and Isobel Campbell, Harry Nilsson, and The Zombies.

Owl and Bear: Do you view any of your bands as side projects?

Al Howard: I can’t afford to look at it that way. If you’re gonna be in a band, you love that entity and you have to put your entirety into it for it to function at its fullest. I was talking to Sean about it the other day at Sands rehearsal. We hit this new song that has an Elephant-era White Stripes feel passed through the filter of a seven-piece band and Heather just absolutely owns it. No one else could sing that song, it would sound wrong on anyone else’s vocals.

I’m a proud parent. I love the similarities and the divergences and the fact that all three bands play their hearts out live. The Heavy Guilt is my first stab at songwriting and the first time someone has trusted me enough to be their lyricist. That’s a really unique bond and it gave me a lot of confidence. Most of my time goes into the Guilt, we play more and get on the road and I live with the singer, but I want everything I do to hit on a certain level or it’s not worth doing.

Owl and Bear: How did you go about recording Awake Now? Did the recording process differ from your other bands’ albums?

Al Howard: We recorded Awake Now at Tim Felten’s (Black Sands, Pocket, Soulfires) house. Everything was recorded in a closet, acoustic guitar first. We added layer after layer and each song kinda revealed what it was going to be with each addition. Doing an album with no drums was a great challenge. I wanted the percussion to support the vocals and not distract from them. A lot of the rhythmic tracks are volume swells on a radio tuned to a non-existent station and run through a space echo. There are tracks where the percussion is two Target bags being rubbed together, me punching a carpeted wall, and there’s tracks of the Normal Heights neighborhood, ran to tape, slowed down, and played backwards.

Tim did a great job accompanying and co-producing, I’d hum a melody and he’d add glockenspiel, Rhodes, organ, or Clavinet. Jason, Josh, and Sean from the Guilt are the backing band which is as good as it gets. Chris Davies from The Penetrators adds some genius guitar and bass parts; he’s one of the most unique players I’ve ever known and his parts are always unexpected highlights for me. Dustin (vocals, guitar) from Old Tiger and Boy King and Aaron Brownwood (Dobro) from The Western Set also guest on the record.

Owl and Bear: The record has a very timeless feel to it. Is it important to you to create music that doesn’t feel beholden to a specific decade?

Al Howard: My favorite era of music is from ’64-’72. Whether it was pop, soul, blues, rock, garage, jazz, or psych, there was a caliber to the musicianship and arrangement that is tough to surpass. The gear, the tones, the experimentation — that era had an echo of the past as well as a vision surpassing tomorrow. I want to make music that has that kind of lasting power. Shelbi has such a special talent, she sounds like she stepped out of another time, at the same time she sounds totally sincere. It is a voice that needs to be supported a specific way and I really feel like we were able to do that tonally.

Owl and Bear: “Good Night” samples the melody of “Amazing Grace.” What was it about “Amazing Grace” that made you want to doff your cap to it?

Al Howard: I didn’t even realize it until Josh pointed it out. Some of these melodies get so ingrained in our subconscious, etched indelibly on our souls, it just felt right there. It used to be a whistle, but we did it with Rhodes and guitar. That song was one of the ones written after knowing Shelbi; it delves into midnight dilemmas about the vast space existing between right and its opposite. That familiar melody and theme is probably something that hits all of us. I wrote a song with the same cadence for the Guilt — that version is based on an episode of Breaking Bad and I hope we get to it soon.

Owl and Bear: You’ve released albums for each of your three bands. What’s next: do you restart the cycle with a new Heavy Guilt album, switch up the order, or start another band?

Al Howard: The Heavy Guilt goes into the studio in December to record our third record. The Pine has about six new songs written so we want to keep the ball rolling. The Sands are poised to record in the new year and Tim, Josh, Rebecca Jade, and I started a soul project that is gonna crush. Hard-hitting soul like Baby Huey Hard Times with a hint of Daptone and Radiohead, so I’m working on that record now. I’ve found my niche in music; it took 10 years of trial, error, and throwing things at the wall. Writing music for different voices gives my pen a different voice as well. I get to be different characters and as a record store clerk I listen to everything. I want to make records that reflect that eclecticism.

Owl and Bear: If you could sing just like Bennet, would you have stepped into the role of singer for The Midnight Pine?

Al Howard: If I could sing like Shelbi that is literally all I would do. I’d sing my sandwich orders to the dude at the cash register, I’d be singing this fuckin’ interview right now. But I love having a voice that sounds like an old man accidentally farting in his plastic-covered rocking chair — I love my role and I wouldn’t want another. No one wants to talk to the sweaty tambourine player after the gig. I can retain my anti-social ways and go home, play Tetris in one window and watch Aqua Teen Hunger Force in another.