We helped Portland songwriter Ashleigh Flynn to get out her latest album, A Million Stars, after falling in love with her songs that rewrote the standard Wild West narrative from a feminine perspective. Knowing that she identified as gay, I was curious to know more about how the characters she found in the Wild West may have related to her own worldview, and how American traditional roots music fit with her perspective. Huge thanks to Ashleigh for being so willing to talk and for being such an engaging speaker!
Gay Traditions Interview with Ashleigh Flynn
Hearth Music: Tell me about the new album. I like that you’re going back to the historical record to look for female heroes to write about. Where did that idea come from?
Ashleigh Flynn: I was walking around in my sister’s basement at the time my niece was around 11, and she had painted what is the cover of my record. She’s grown up in Portland her whole life and didn’t know much about the Wild West or cowgirls. I just thought it was cool that she imagined herself in that environment. I started to think about… “What if it were me growing up in that era? How would I have possibly fit in because I definitely would have been more of a Calamity Jane character than a madam at a brothel or a preacher’s wife who tried to settle the prairie. So, I dug into the annals of history and I didn’t find a bunch of stories about people like me, but I found some. That’s where the album’s title song about Cattle Annie and Little Britches emerged and that started a line of inquiry, the whole melody and tone for the record.
Ashleigh Flynn: A Million Stars
That’s interesting. Usually people are looking for a strong, female character in the West but you were specifically looking for women who might have been lesbians or might have been gay or you felt were similar to you as a person?
AF: They probably had no idea that they were lesbian or gay; that probably didn’t get talked about. I don’t know, but I couldn’t find much about the topic of queerness at least in the stuff that I was reading. There’s all kinds of different accounts, but nowhere did they talk about anybody as being gay. I would venture to guess that there were plenty of women who were gay and there were plenty of men who were gay.
That’s interesting that some of the women would dress up as men. There’s a lot of that in songs from all over the Western world that almost seems that might be code that there’s something more going on than just wanting to be accepted in a man’s world.
AF: I would think that it’s a signal to others like them. We talk about “gaydar.” “That guy must be gay or he looks gay or I can sense that that person’s gay…” I imagine that that happened back then and that people who were of that same biological set, that they could recognize each other. In my version of it, Little Britches is the butch and Cattle Annie, while she dressed like a man, was probably more the fem because she ended up marrying an Indian and continuing to peddle whiskey, whereas Little Britches got sick and died as far as I could tell from what I read.
Did you feel that when you were looking at the Wild West, there was more of a tolerance for people who were outside of the norm than in other parts of the nation at that time?
AF: Yeah. If you were strong and could survive; I think it was the survival of the fittest. If you were a woman who had an inclination to live in the same way that the men were, like outlaws, then you had to be strong and you had to be able to wield a gun and you had to ride a horse and you had to know how to take care of yourself. I think it was more about survival of the fittest and I think that there was all kinds of intolerance but it wasn’t as institutionalized because that part of the U.S. wasn’t settled yet.
That’s an interesting theory. What about the song, “Prohibition Rose”? That’s another song that is based on an historical figure?
AF: Yeah. She’s sort of shadowy. She supposedly lived in Portland during the Prohibition era and she was pretty rough. Have you heard of the Shanghai Tunnels down here? They were underground tunnels. For example, at the White Eagle Pub, which is owned by McMenamin’s, which is in lower Northeast, there is an actual tunnel that runs from the basement of that pub down to the waterfront. There are all sorts of them across inner Portland. It was a smuggling route; they were ways of smuggling opium in from China, and smuggling other things out. She could bring her booze in that way, she could bring opium in that way. The story went that she ran all these speak-easies. She would get the fellows, mostly sailors, drunk by day as they were waiting for work, and, if she didn’t like you, or you got messy in her bar, she’d get you really wasted and you’d pass out. Then she would send you down to a holding area in the Shanghai tunnels, they would smuggle you out, and you would become forced labor on a ship. But she was one of the wealthiest booze dealers during Prohibition and she was a woman. I thought that was kind of interesting. She was constantly evading the cops.
Ashleigh Flynn: Prohibition Rose
A gangster heroine but she was more of a kingpin than a sidekick.
AF: Yeah, she was more of a kingpin. She was a racketeer and the story goes that she got wind of this big thing that the cops were trying to pull on her while she was at one of her speakeasies. I don’t remember what her cover was but the cops busted into her place and before they did, she had all of the guys that worked with her and drank her brew throw all the whiskey bottles under her big, old skirt and she sat there in the middle of the room and swore on a bible oath that there was no alcohol. Then, when the cops came in, they weren’t going to dare look under her skirt. I don’t even think they thought to look under her skirt.
[laughing] That’s a great story. How does it feel to go looking to try to find yourself in the history of the music. Do you feel like it brings you closer to the music that you sing and perform?
AF: I feel that this record, the story finding and the story making, really did. I still think that roots music and most music, maybe not pop music, is a male dominated field but the people that I like are making so much good music and it’s really what comes out of me. Americana is my natural voice.
Has this changed since your earliest work? Do you think that you’ve moved more to
the roots end of things?
AF: It’s funny. My first record was pretty roots and then I started experimenting and got mixed up with a bunch of engineer/producer folks who really liked to do production layering. I diverged off what was my true path but I think that I’ve honed my songwriting more towards an Americana/roots vein and it feels more authentic. It feels truer to me. It feels more natural in its delivery and the way that I’m writing. I’m working more on the songs as stories.
Did you grow up around this music in the South? Did you grow up around real twang-heavy music?
AF: Yeah. I grew up in Louisville, Kentucky and I spent many weekends down at a place called the Belvedere, listening to bluegrass music. Sam Bush used to live there and was honing his chops. We went to all kinds of bluegrass festivals; I grew up on Willie Nelson.
So tell me about the Portland scene. How did you meet up with Chris Funk of Black Prairie and The Decemberists? What was it like working with him?
AF: I met up with Chris over 10 years ago in Eugene, Oregon. We had both moved to Eugene and I had just started writing songs because I had all this time on my hands. I was living in a cabin and my friend had died and I had written a song of mourning for him. I went down and I played it at an open-mike and the owner of the coffee shop offered me a regular gig and I literally knew 4 songs. I was playing the gig and Chris had just move to town too and he showed up. He came up to me after I was done and I think I played the 4 songs I knew probably 3 times each to get through the gig. He introduced himself and offered to buy me a beer and asked me if I needed a side guy. We became fast friends and he inspired me to make my first record and then he went on and became famous. I did music here and there and then got serious about it with my last record and we’ve been friends all along but I never imagined I’d get to work with him, so I was really stoked. It was fun! It was fun and he’s really a creative guy.
And he brought some great musicians along too.
AF: Yeah, totally. I was really stoked to have them all but it’s impossible for me to tour with a band because they’re all taken up.
Portland seems really down-to-earth. High profile people like Chris seem really supportive of the scene. Do you think that’s the case?
AF: I think, with him particularly, that is the case. He is extremely generous of his time and extremely supportive. There’s all kinds of music that goes on here and he has his hands in all kinds of different projects. His group of friends, my group of friends, they’re all really successful in their own right and all the players on my record are very generous people, the Black Prairie folks, The Decemberists folks.
How long have you lived in Portland?
AF: A little over 10 years.
What brought you to Portland and the Northwest?
AF: I did the AmeriCorps Program outside of Eugene for 2 years. That’s when I lived in a cabin and started writing songs. I didn’t really become serious about music until I put my last record out which was called American Dreams. So, I came up to Portland to get a job as a grant writer in non-profits and I was playing gigs and having fun and I didn’t think much about touring or anything like that. About 5 years ago, I was like, “Wow! I’d really like to travel and be a troubadour and be about that.”
Did you quit your job or do you still work as a grant writer?
AF: I still work as a grant writer part-time.
You’re from the South. Where did you grow up in the South?
AF: In Kentucky and Virginia.
How long did you live down there?
AF: All through my high-school years and then I moved to Colorado for college and I met a bunch of great musicians out there and started learning how to play guitar. Then I moved out to Oregon.
I talked with Emily Herring for this Gay Traditions series before. She’s gay and she’s a really excellent honky-tonk musician. She saw Portland as a real haven. It was a place where she could feel really safe and her identity was welcomed. There were a lot of other people that she could connect with who she personally felt a connection to and she saw it as an oasis. Do you feel the same way about Portland as compared to where you grew up in the South?
AF: Oh yeah. As far as its politics, it’s totally liberal and accepting and welcoming. It is an oasis in that respect.
When did you come out and how did you reconcile that with who you were at the time?
AF: Being gay? It was when I came out here. I struggled in college a lot because I didn’t grow up with any gay anything. In fact, most of my family and my peer group were uber-straight and creeped out by the whole notion of gayness, but none of us had any experience first-hand. I didn’t have any gay friends, at least that I knew of, through high-school or college. I ended up falling in love with my best friend and we ran away to Oregon, both looking to find careers in non-profit and also to get a chance to figure it out. I actually came out when I was living in Eugene and it was fine. Everybody was like, “Great! Cool!”
You were living in Eugene! Eugene is even more liberal in many ways than Portland.
AF: Yeah, totally. It was really easy. It wasn’t easy in college because I faced some rough stuff from folks and so I felt a lot of guilt and shame for that period of my life. I really regret that. I regret not being stronger in myself but… we all have our own paths.
How did your family react to the news?
AF: They were fine with it. It took them a little time to adjust but now they totally embrace it. They think it’s great!
You didn’t grow up in a Southern church-going family necessarily?
AF: No. I had some of that influence from my surrogate grandmother but my parents were atheists.
How did your grandmother react to the news then?
AF: She was fine. She was my surrogate grandmother; she’s a woman who raised me and we would go to the Baptist church, but it wasn’t like I had the bible beaten into me and the fear of the devil. I did all that stuff to myself, just freaking out.
What do you mean, you did all that stuff to yourself?
AF: I’ve always been a very serious person and the big questions have always plagued me like, “Why are we here? What are all these stories about religion?” and right around the time when I was trying to figure out who I was, I got really freaked about going to hell. It was a manifestation of feelings of guilt and shame but really powerful emotions.
How did you get beyond that? How did you find your way past that?
AF: Opening up about being gay really helped. I still freak out about the big questions but not in a way that I’m freaked out about hell. I was able to realize that those are stories and scare tactics to try and control people of old… the bible, the stories in the bible. I just evolved past that by realizing that it was somewhat irrational, given the context of my life and all of the blessings that have been bestowed on me. I’ve got great families, I’ve got health, I’ve been able to spend time writing songs, and traveling the world playing them. I just evolved past it.
With the “It Gets Better” movement now… Do you think that would have helped when you were younger? Knowing that there were other people struggling with this, and other role models out there?
AF: Oh, totally. I wish that I would have found something like that at my turning point. I went to a pretty dark place for a good couple of years feeling like I was trash.
There’s a lot of work now with teens who are LGBT, connecting them to other teens, and connecting them to role models. Do you think that the kids who are coming out today have a lot better time than you had?
AF: I would say yes and no. There was a kid this year in the Dalles in Eastern Oregon who hanged himself for being bullied. That’s heart-breaking but I hope that they are having an easier time. I think that it’s a much more visible culture in high-schools and in colleges. I think that there’s a lot more support but I still think that there a lot of ignorant, intolerant people who pass judgment and worse. So there’s still work to do.
What advice would you offer young kids coming out today?
AF: To try and connect with your GSA at school because what you need is friends and support. GSA—that’s a good starting place.
What’s a GSA?
AF: It’s a Gay Straight Alliance. Most schools have them and if they don’t, to try and find a resource center. There’s a lot of them all over the country. In fact, I work for one here in Portland.
Tell me about Todd Snider because he’s a big part of the album. Did you meet him in Portland?
AF: No. I just got hooked up with him on some shows via a friend of mine in Nashville, very last minute, after I had put my last record out and I had such a great time playing for his audience. It was my first couple of big shows and so I just kept in touch with him and we became friends and I kept seeing if there were shows that I could do with him and he kept having me come. So that’s been nice. He’s really helped me get out and play shows. He really is supportive of who I am and all gay people.
How did you bring him on to the record?
AF: I just asked him because I had made up that song, “See that Light” and I kept imagining the kid, and the kid being me, who was trying to find their way and maybe they keep falling in love and realizing, “Shoot, I can’t have this kind of love because it’s not allowed or it’s dirty or I’m going to get beat up or that person’s never going to love me because they’re straight.” I imagined that kid always having to hold love at bay and ultimately, doing harm to themselves. A higher proportion of kids who are gay, drink and do drugs and commit suicide. The song’s really light; it plays with that notion of being in love with the moon and the moon is totally inaccessible. I kept hearing this talking-blues part over the top and it was a Todd Snider type of a rant that he goes on at his live shows which I love. He’ll tell a story; he’ll go on and on about something, and then he’ll bring it right back around to the song. It’s brilliant! I tried to channel him a little bit and he thought that was a cool idea. It was really cool!
Ashleigh Flynn: See That Light feat. Todd Snider
Thanks again to Ashleigh Flynn! Pick up her new album, A Million Stars, at CDBaby:
