A few years ago, while wandering in one of my favorite spots for solitude, a little red truck drove by. I felt a flicker of annoyance when it stopped and the driver began talking to me. To my surprise, he showed me how his dog could “drive” — a playful stunt that caught me off guard. Then, he pulled out his guitar and played a song, turning my annoyance into amusement. Naturally, I asked if I could photograph them.
Every time I look at those photos, I can’t help but laugh. I knew I had to paint the moment of the man playing his guitar while his Chihuahua squinted at me.
Jackson, Ann. (2026).Chihuahua Chauffeur. [Acrylic mixed media on cradle board]. Available.
1 x 14 inch
A friend sent me a photo of identical twins sleeping, with a single curl between their heads that seems to bind them together. I recently returned to oil painting and seized the opportunity to practice on an old canvas. I’m pleased with the results, which evoke a charming children’s book illustration vibe.
Jackson, Ann. (2025). Bound by a Curl. [Oil on canvas]. Available. 20 x 16 inch
The glow of the street light filtering through the blinds creates a captivating play of light and shadow on the nude body. The interplay of illumination casts intriguing shapes, accentuating the curves and contours of the figure. As the light dances across the skin, it produces a spectrum of warm colors, illuminating the space with a soft, ethereal ambiance. This beautiful juxtaposition of harsh external light and the delicate form within invites the viewer to appreciate the artistry in the way light interacts with the human silhouette, transforming an ordinary moment into a visual poem of shapes and hues.
Jackson, Ann. (2025).Blind Date. [Acrylic on canvas]. Available.
11 x 14 inches
For the first time in decades, I experimented with oil painting. It proved to be much more challenging than I remembered from my early days as an artist. I appreciate how oil paint allows for easier blending compared to acrylic or watercolor, making it an ideal medium for nude paintings. However, the clean-up process is definitely more complicated.
Jackson, Ann. (2023).Untitled Nude. [Oil on canvas]. Available.
11 x 14 inch
After an evening out with friends, where I enjoyed three beers—one more than my usual limit of two—I found myself brushing my teeth topless while gazing in the mirror. The way my hair draped over half of my breasts sparked a memory of the Lady Godiva story. Naturally, I took a photo with my phone. Eventually, I transformed that image into a piece of art.
Jackson, Ann. (2022). Red Curtains. [Acrylic mixed media on canvas]. Available. 12 x 16 inches
I was commissioned to create a pair of horse head paintings, with the backgrounds already completed and sketches underway when my client and good friend suddenly passed away.
A couple of months later, while examining the background of one canvas, I noticed it resembled denim. A smile crossed my face as I realized my deceased friend would appreciate the fact that I painted a denim-clad booty (my own) against his horse head background. And that’s how Cornbread Booty came to life.
As for the title? It’s a nickname given to me by an ex-co-worker. (Thanks, Zennia!)
Cornbread Booty needed a companion, so I created Lucky You to complete the pair.
“RIP Richard! You are missed tremendously, and I know you would be delighted with the outcome of your paintings. I can hear you saying, ‘Well, that’s what I really wanted but wasn’t going to ask.’”
Jackson, Ann. (2021). Cornbread Booty. [Acrylic on canvas]. Chattanooga, TN: Private collection. 10″x10″ Jackson, Ann. (2021). Lucky You. [Acrylic on canvas]. Chattanooga, TN: Private collection. 10″x10″
This stockinged beauty emerged from the painted background, inspiring me let her shine through. She appears sun-kissed, evoking the essence of warmth and joy, much like Bob Seger’s song “Sunspot Baby,” which played on repeat in my mind as I worked on the piece.
Jackson, Ann. (2020) Sunspot Baby. [Acrylic on canvas]. Chattanooga TN: Private collection. 16″ x 20″
Sunspot Baby by Bob Seger
She packed up her bags and she took off down the road Left me here stranded with the bills she owed She gave me a false address Took off with my American Express Sunspot Baby She sure had me way outguessed
She left me here stranded like a dog out in the yard Charged up a fortune on my credit card She used my address and my name Man that was sure unkind Sunspot Baby She sure had a real good time
I looked in Miami I looked in Negril The closest I came was a month old bill I checked the Bahamas and they said she was gone Can’t understand why she did me so wrong
But she packed up her bags and she took off down the road She said she was going to visit sister Flo She used my address and my name And man that was sure unkind Sunspot Baby I’m gonna catch up sometime Sure had a real good time
I looked in Miami I looked in Negril The closest I came was a month old bill I checked the Bahamas and they said she was gone I can’t understand why she did me so wrong
But she packed up her bags and she took off down the road She left me here stranded with the bills she owed She used my address and my name And put my credit to shame Sunspot Baby Sure had a real good time
Oh, Sunspot Baby She sure had a real good time Yeah, Sunspot Baby I’m gonna catch up sometime Sometime, oh
Gonna track you down, oh
13 You were in Eden, the garden of God; every precious stone adorned you: carnelian, chrysolite and emerald, topaz, onyx and jasper, lapis lazuli, turquoise and beryl.[a] Your settings and mountings[b] were made of gold; on the day you were created they were prepared.
14 You were anointed as a guardian cherub, for so I ordained you. You were on the holy mount of God; you walked among the fiery stones.
15 You were blameless in your ways from the day you were created till wickedness was found in you.
Jackson, Ann. (2015). Vexation. [Acrylic watercolor on paper]. Soddy-Daisy, TN: Private collection.
30″ x 22″
Dear John,
After careful consideration, I have decided things are just not working out between us. I made certain guidelines for myself years ago and, quite frankly, my boyfriend looking better in a dress is one of them. So I’m afraid it’s over.
Sincerely, Ann
P.S. Kindly return all my clothing you borrowed
My friend Laura jokingly suggested the above words for the letter after I mentioned wanting it to be a “Dear John” letter but wasn’t sure what to write. She found it hilarious that I actually used her suggestion in the painting.
Jackson, Ann. (2015). Dear John. [Acrylic watercolor on paper]. Soddy-Daisy, TN: Private collection.
30″ x 22″
Babylon as the quietly aching mother of all abominations. Judas kisses of the final death sparking behind her eyes with the original sin of the first come hither glance that leads to utter destruction. Composed lips of seductive million Hiroshima. (written by Zach Burnette)
Jackson, Ann. (2014). Babylon – Stealer of Souls. [Acrylic watercolor on paper]. Soddy-Daisy, TN: Private collection.
