The Art of Life, Ashley Longshore Style

Telling it like it is...

Everything about Ashley Longshore is larger than life. Her personality, her sense of humor, her talent, her career, her art – and her heart. Bodacious and bold in thought and deed, she is a force of nature not easily deterred or encountered, a once-in-a-lifetime phenom who roars into view with a confidence and calling few can claim. An entrepreneur, self-taught artist and sculptor whose work speaks as honestly and openly as she does, Ashley dislikes pretention, champions independence and embodies success, parlaying her preference for private jets in tongue-and-cheek comments impossible to ignore.

“Sometimes you just have to tell it like it is,” admitted Ashley when I talked to her for this article, making a mental note to stay true to my words and intentions like she does, or at least try. After all, she has made her living speaking and painting her mind, without worrying about consequences, controversy or failure. It’s not in her DNA to give in or give up, self-defeating behaviors she dismisses with disdain.

Born in Alabama and raised with southern sensibilities, Ashley set off on her own path, choosing to follow her dream of being an artist rather than marry money as her parents hoped.

Rejecting the prescribed future of a sweet southern belle who demurred to the men in her life, Ashley knew she was different. “I knew I wanted to be independent. I knew that I wanted to be great. I didn’t really come into my art until I was around 18 years old. I started painting after my parents had gotten a divorce, and I found a great love of my life on that day, a great love that made time stop,” she explained. “When you go into that portal of creating and painting, the rest of the world absolutely disappears, and it is a very safe, beautiful place to be. As a young girl who didn’t necessarily know what my future held, I found great, great power and security in painting. So I did it all the time, and one day I stood back, and I’m like, ‘I have a room full of paintings. I should sell them. You know, I could make a living doing this.’ That’s also when you get tough too, because you get a lot of rejection. You get a lot of people telling you that you’re never going to make it. You get people telling you that you’re not marketable.”

Instead of listening to that inner monologue that agrees with the naysayers and breeds insecurities, Ashley followed her own voice – and the world took notice.

Ashley has “always loved color,” she told me, adding that she started her career with figurative work. The first time she added her signature text to her paintings, it appeared as tiny handwritten letters.

“But then I did a series where I brought in really bold text, and I was like, Ooh, I like this. This is in your face. This is bold. This feels like me.”

Supermodel High Kicks, 72 x 60in, Acrylic on Canvas, 2024

Hailed as the feminine Andy Warhol of today’s pop culture artists with a huge cult following, Ashley’s art, bursting with joy, color, comedic undertones and real talk, moves collectors, celebrities, fashion houses and publishers like few others have. Her work speaks volumes about positivity and possibilities, drawing audiences in with uncensored expressions about consumerism, the American dream and cultural mores. She paints her personality into portraits of wonder women, similarly empowered with Ashley’s drive for success, feminine freedom and desire for independence. Bejeweled images of glamour and glitz dazzle with fabulous ideals, details – and digs. And storied depictions of flowers, bunnies and birds pulse with life as she experiences it. Outspoken and introspective, her entire portfolio – online and gallery-free – is a uniquely distinctive, ultimately whimsical celebration of the things this deeply caring artist holds dear.

Lest you think she had a hand up, think again. Ashley didn’t come by her fame by happenstance. She worked hard for it, without comprising her values, her drive or her boundaries.

“When I wake up in the morning, I don’t tell myself why I can’t do something. When I think of my goals, I don’t sit there and think about why this is going to be impossible. I wake up, I work as hard as I can, and I create. I have an incredible team around me. We have a vision of putting art out there spreading joy, and above all things, the inspiration that the weirdest thing about you is probably the greatest thing about you, and that is your superpower. That energy, along with being enthusiastic and grateful, opens a lot of doors.”

Photo by Mary Ellen Matthews

“The first time somebody spent $100 on one of my paintings, I realized how awesome it was to be financially independent. That was my first big break, the opportunity we live for. We live for great ideas, and we live for opportunities to share those ideas. I understood then that you don’t have to be dead – or a man – to make it as an artist. There are so many successful men and male artists out there, and I thought, why can’t I be a very successful female artist?”

Ashley, never one to hang on the coat sleeves of men who make promises for pay, made her own opportunities – and her own money – on her own terms. Of course, she faced rejection, lots of it, she told me, but she shut out the discouraging words and kept on going. She represents her art herself, eschewing galleries and their exorbitant commission rates, and marketing her work online and in her own gallery in New Orleans, before moving it to New York City where her already huge career typhooned.

“That inner monologue is a very important thing because people can smell fear, and you really have to be confident. It took me 30 years and 10 months to be able to have my gallery in New York, in Soho. 30 years and 10 months I worked to be able to have this, to be able to get to this place where I have more opportunity and connectivity in the greatest city in the world, a conduit to the rest of the world, a city that is great not because of hedge fund guys and lawyers, a city that is great because of art and theater and poetry and food and dance. That’s why people love it here. That’s why I love it here too.”

Photo Credit Harol Baez

New York, not surprisingly, loves her too. She is the first solo female artist to have her work featured in the Fifth Avenue windows and seventh floor of New York’s famous Bergdorf Goodman department store. Her collector clients include actresses Blake Lively, Salma Hayek, and Penelope Cruz, NFL quarterback Eli Manning, and Wall Street’s elite. She has collaborated with luxury brands Chloe, Anthropologie, Gucci, Porsche, Maybelline and Judith Leiber and she hobnobs with A listers from film and fashion, Oprah, Tommy Hilfiger, Diane von Furstenberg, Christian Siriano and more without raising an eyebrow. She’s laughed it up with Seth Meyers on late night TV, showcasing her off-the-cuff, stand-up comedy humor to ovation-worthy applause. Naturally funny, often irreverent and fabulously uninhibited, she could have another rising-star career should she care to make it her own.

Ashley Longshore’s latest book: Giving the Bird

Her art has been published in three books, including You Don’t Look Fat, You Look Crazy: An Unapologetic Guide to Being Ambitchous; I Do Not Cook, I Do Not Clean, I Do Not Fly Commercial; Roar, A Collection of Mighty Women; and Giving the Bird, newly published by Rizzoli in September. Giving the Bird is an irreverent collection and character study of whimsical painted birds, whose unique personalities are described in accompanying imaginative write-ups by the author herself. The book is pure Ashley: hilarious, over the top, in vivid technicolor and, like all of her work, promises to put you in a great mood.

Whatever her endeavor, Ashley hopes her legacy inspires others to do what they want, fully, completely and authentically. To that end, she has established a foundation that awards unrestricted financial scholarships to emerging artists so they can follow their dreams wherever they take them.

“I think the main thing that artists live for, other than the time to create, is opportunity. That’s why I choose to give unrestricted money to them through their scholarship awards. Artists need money. I’m not afraid, as a woman or an artist to say, I like to make money. If I have money, I can travel all over the world. I can be inspired. If I have money, I can help the creative community and keep this energy flowing. If I sell a painting, that means I can go buy a painting from somebody, and that is the life that I want to live. If an artist that I help through my foundation needs to pay their rent, they can take that money and pay their rent. If they’ve been wanting to go to Europe to look at incredible paintings from the Renaissance, they can take that money and go. These are very ambitious, hard-working artists that are dreaming of making it big. They’re at the emerging part of their careers, so they can take that money and do whatever they want with it. I’m just here to help provide them with what they need to thrive. They wouldn’t have the opportunity to win that Art in Excellence Award without being very ambitious and driven in their in their practice.”

The money Ashley has made, all of it by her own hand, has enabled her to live the life she dreamed of in ways that make her happy and bring her abundant joy. From the talking art she creates from the moment she wakes up to the Louisiana farm where she and her husband relax, unrestricted and often au naturel, dogs, chicken and nature front and center, to the private planes she jets about in and the bling she wears as she celebrates her fantastical career, Ashley is exactly where and what she wants to be.

With the entire planet as her palette, the inspiration for her art plays out in her real-life experiences, ones that are as fun, fanciful and fearless as she is.

Photo Credit Harol Baez

“Not too long ago I did a painting of a huge Sapphire, with the words, ‘The harder you work, the luckier you get.’ It’s just so true. Danielle Steele saw that painting when she came into my gallery and said, ‘That’s so funny. Everybody thinks it’s just luck, but it really is hard work to keep creating.’ Danielle is a big collector of mine. She’s such a fabulous woman. She just hit over a billion books sold, by the way, and is still working and probably will be writing until her last breath. I have so much respect for her, because I think I will also be that way. I know I’m not going to stop creating art until I’m dead and gone. I also think about the different roles of being a woman in society. I think about my disdain for the patriarchy and being undervalued as a female artist.”

Women like Danielle Steele and so many others share Ashley’s back story of hard work and sacrifice, dreaming of enjoying the fruits of their labors when their ships come in – and finding hope in Ashley’s evocative art.

“I just wish for financial independence for women. For me, the idea of sucking up to a man so I can have permission to go buy a purse just sounds awful. So, you know, I play with that. I play with status. I play with pop culture and my role in it. I do in a provocative way. It’s sort of how I am with politics. Anybody with a brain in their head can definitely see that I’m a feminist. I painted RBG, and just posted a picture of Kamala Harris in front of one of my Wonder Woman paintings that Linda Carter had requested from Diane von Furstenberg. The thing is, I believe in women. I vote for women and gays. I paint these incredible women because when I am surrounded by them, they make me brave. They’ve all taken a bunch of shit from society, and what they’ve been able to do is say, F* that. I know who I am. I’m going to be me, and I’m going to be me relentlessly, no matter what the world throws at me and that makes me brave.”

The Hotter the Fire the Stronger the Steel, 60 x 60in, Acrylic and Gold Leaf on Canvas, 2024

That bravery is like a magnet for collectors, celebrities among them.

“I’m fun, which is why I am able to meet so many people. I’ve always been able to put myself in a place where there were successful, notable people. But truly, my greatest collectors are women who have been saving their money for a year to come in to buy a piece of my artwork. That means a lot more to me because I celebrate them. And you have to know, nobody’s given me anything. When I didn’t have two nickels to rub together and somebody bought a $500 painting from me, I celebrated, just like I do today. Let’s party! Let’s dance!”

As someone who spends 8 hours a day sleeping, 8 hours working and 8 hours to just be, what advice does she share with emerging artists and the women she so wishes would succeed?

“Always be true to yourself. The only way that you will fail is if you quit. That need for instant gratification is a tough one, because instant gratification gets you high, drunk or pregnant. Everything else takes a minute.”

“Surround yourself with what you love. When I eked out $500 for my first little apartment, I wanted it to be artful. I wanted to surround myself with that energy. So I’d go to museums and galleries, and I would always have a little bit of money to buy something artful and cool that I could have in my space. I just surround myself with art, with other people’s art. If I sell a painting, then I go and buy art. My dream is to have a career like Andy Warhol and leave a legacy like Peggy Guggenheim.”

She’s already checked off the first box, big time, and is well on her way to leaving a legacy that can only be attributed to Ashley Longshore.

“I want to have a space where I have my personal art collection openly displayed for the public to visit. I love fashion, and I have some really, really great pieces, so I would want to have those there as well, and then have a whole floor where my foundation could continue to showcase emerging talent and bring in people to speak to artists. Above all things, right where you walk into the foundation, I want to be waxed like a pope in a glass box. And people will come in and they’ll cry and they’ll leave flowers and there’ll be candle drippings everywhere.”

Leaving me laughing as we ended our chat, Ashley told me that her birthday was the next day.

She had a cake made of her breasts and the c-word printed in big red letters.

“Who would do that? In my mind, this is the perfect birthday cake for me and I’m serving it to all my friends. What’s wrong with me? I have a bad gene, but it’s marketable. You know, I’ve been on red carpets, I’ve been on private jets, I’ve bought Birkin bags and all that stuff, and it’s great. But there ain’t nothing like driving your golf cart topless. That’s joy, right there. The rest of it’s a machine. It doesn’t get better than that.”

www.ashleylongshore.com

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