David Nail Delivers Remarkable Songwriting On ‘Bootheel 2020’ EP

David Nail first heard the term “roach motel” in high school, and he always thought it was simply a distinction for a rundown motel on the outskirts of town. Through what he describes as “cut down wars” with his friends ─ hurling insults like “your mom is this” or “your dad is that” ─ he knew it had a negative connotation, particularly as it relates to sex workers.

With his song “Roach Motel,” Nail paints an emotional story about a sex worker, and he does so with beautiful dexterity, making sure to depict her humanity and strength through terrible tragedy. “She said, ‘I was 13, barely out of seventh grade, and that summer every boy kept coming around my way,” he sings over stunning piano. “I’ve been in your shoes / Don’t you worry ‘bout a thing / Ain’t nothing you can do / That I ain’t ever felt or seen.”

Nail lets the listener fill in the blanks; you don’t necessarily need every single detail to understand the song’s central theme. He simply unravels a narrative “about this girl who in reality is every bit of a victim and who, right or wrong, in her mind has turned the tables,” he tells American Songwriter over a phone call earlier this week.

“‘Guess now I find comfort here on the other side / Always knowing I’m a memory / You ain’t the first, and you won’t be the last / To be with me / For a moment, be with me,’” he unpacks brutal heaviness on the bridge.

“Roach Motel,” anchoring his brand new EP Bootheel 2020, borrows elements from a very real story Nail was told. On first instinct, he considered writing around “all those stereotypes and those negative thoughts [that are] too often people’s first thoughts,” he explains. “When I finally allowed myself to hear the entire story, I don’t know if I so much felt sorry for her, but it made me respect the hell out of her. I had this admiration for her and how strong she had to have been to still be standing.”

“I just want to hug her and say, ‘You’re loved, and it’s not your fault. And I don’t blame you for doing what you do or feeling what you feel. You didn’t ask for this,’” he adds. “A lot of times, we see certain things or hear certain stories about people and you have that first reaction ─ and that’s all you allow yourself to believe or think. You don’t necessarily think about the journey and how [that person] got there.”

Nail’s new EP, produced with Reed Pittman, follows his 2019 release, Oh, Mother, on which he addressed matters of the heart and mental health. “That’s the cool thing about being an independent artist: you can march to the beat of your own drum,” he says.

Nail began writing the project at the start of the year with the intention of perhaps releasing a string of EPs. Of course, the world had other things in mind. Instead, he shelved the songs and didn’t revisit the idea until about a month ago. He realized if he “didn’t get it out this year, it probably would have never come out or would have drastically changed,” he says.

“There’s a very cinematic aspect to this music. The songs all came to me within about a month’s time. That’s really how I’ve always worked. When I write by myself, they usually come in bunches. And then you can’t think of anything and you feel like a loser for several months after that,” he continues. “Each title is very elementary, but with that, it allows you the opportunity to go anywhere. Having that freedom allowed me to create a story that ended up being very specific to the title and very specific to me.”

“Back Home” certainly leans into his own deep longing, missing his parents and a simpler way of life. “I was just 17 / Couldn’t wait to get out / Had much bigger dreams / Bigger than this ole town,” he sings, guitar in tow. The arrangement dances around his voice like rays of sunshine, managing to be both wistful and hopeful, and Nail dishes up one of his best vocal performances to-date.

On the other end of the musical spectrum, “Nobody Knows” slides along with an otherworldly spookiness, equal parts synthetic and organic. “Secrets fade into the wind / They won’t find a trace,” he whispers through layered drum patterns and dark synth work. “Why can’t they be colorblind / Break from the chains of hate.”

One day, while fiddling with finger patterns on the guitar, he stumbled upon a structure he wasn’t “used to or familiar with,” he says. “There was an immediate tension to it. I feel I’ve always trusted myself, and I’ve never pursued things because they sounded different. I wrestled with that for a while.” 

It was the weekend before lockdown when he’d been out in L.A. playing some shows. After a few drinks, he played Pittman and his tour manager a rough worktape of guitar and vocals on their way to the airport. “I was feeling proud at that moment and wanted to play it and get that initial reaction,” he recalls. Needless to say, Pittman liked it within the first few lines, and Nail soon set about finishing it. “If I don’t finish something soon after I start, I start to force it. When you try to force it, the song can suffer and fall flat.”

“I remember coming to the chorus and thinking, ‘Well, I surely can’t keep repeating this. This is ridiculous.’ As it grew on me, and more time went by, it started to feel like the more natural thing to do. There were times in my life where I would have thought, ‘Man, that guy just kind of took the easy way out.’ As long as I’ve been doing this, one thing I’ve learned is that sometimes you can outsmart yourself or try to outsmart yourself.”

He gave himself permission to follow the muse wherever it led, trusting himself the whole way. When he was listening to SiriusXM’s The Spectrum station, he heard a song that immediately struck him, and it lead to one of the song’s most crucial puzzle pieces. “I picked up my recorder and recorded the sound of this drum loop. I texted it to my drummer and said, ‘Do you think you  could recreate this with real drums?’” he says. 

An hour later, Matt Iceman sent over three different drum patterns. “I flipped out,” Nail says with a laugh. He called up Pittman the next day, sent him the song files, and set to working out the vocals. “I’m literally singing this song in the order [Matt] sent me the files. Where he picks back up in the chorus is a very unnatural place to do it, but that’s where I was in my car singing what I had over this loop.”

The original guitar pattern was swapped for a Rhodes piano sound, and the bass part shifted to “the fakest bass sound in the history of the world” to boost the song’s slithering undercurrent. “It was just before Halloween, and my son had fallen head over heels in love with Michael Jackson’s ‘Thriller.’ I was listening to the song, but I started listening to that record. As soon as Reed came up with [the bass line], I told him it sounded like it could be on ‘Thriller.’”

Nail’s Bootheel 2020 contains three new originals ─ woven together with a prelude and interlude, both spoken word pieces performed by his son Lawson. Initially, Nail toyed with having him perform actual song lyrics or a cherished hymn, but nothing felt quite right until they were hanging out together one afternoon.

They’d been sitting around chatting about Nail’s parents when Lawson started asking questions about his upbringing in Kennett, Missouri. “I grabbed my phone and the voice recorder, and we just started talking. I asked him three or four different questions,” Nail shares. He then used “actual conversation” for the two setpieces, unexpectedly becoming the glue to hold the project together.

“It hit me like a pile of bricks. It’s weird,” he describes. “It’s one of those things had I really put a whole lot of thought into it, it definitely would have sounded staged. I feel it comes across very naturally. Being on the spot, you have that pure emotion and reaction from him.”

As one might imagine, this creative process got him thinking about family and fatherhood in a fresh new way. “I see a lot of myself in him. Sometimes, that’s not always a good thing. He’s very much in that curiosity phase, and he’ll ask you a million questions,” he offers. “One of the things my wife and I have tried to make sure he realizes and appreciates is that he’s named after my grandfather. That was always very special to me ─ to be able to pass that down.”