My brilliant wife Tara is on the cutting edge of AI developments and sends me things from time to time because I can barely keep up. Today she sent me this, and being an artist who simultaneously loves/hates knowing what anyone thinks of my work, I had to try it immediately. This is the prompt:

Assume the role of a stringent art critic with a discerning eye for quality and technique. Your task is to evaluate artworks with precision, providing scores on a scale from 1 to 10. In this scale, 1 represents art that lacks any technical skill, creativity, or emotional impact, often seen as amateurish or poorly executed. A score of 10 is reserved exclusively for artworks that exhibit exceptional mastery, innovation, and depth, setting new standards in the art world. Be meticulous and honest in your evaluations, consider factors like composition, color harmony, technical skill, originality, and emotional expression in your critiques. Remember, a high score is earned through genuine artistry and profound impact.

I figured I’d start this off with two of my most well known photos, not only because I wanted ChatGPTs approval (I do) but because I’ve heard enough people talk about these images over the years that I thought I’d have a good frame of reference for how GPT was thinking about them. So let’s see:


Composition: The way the artist has captured the bird in mid-flight amidst a busy cityscape is commendable. The blurred background not only accentuates the focus on the bird but also brings out the contrast between nature and urban life. The diagonal flow created by the bird’s trajectory juxtaposed against the bus adds a dynamic feel.

Color Harmony: As this is a black and white photograph, color harmony pertains to the tonal range. There’s a good distribution of blacks, whites, and greys, giving it depth and dimension.

Technical Skill: Capturing motion with clarity while blurring the surroundings requires skill, especially in a bustling environment.

Originality: The idea of capturing nature in urban settings isn’t entirely new, but the execution here is distinctive.

Emotional Expression: There’s a sense of freedom evoked by the bird in flight juxtaposed against the constraining city background. It’s a fleeting moment of nature amidst chaos.

Score: 8/10

Composition: The intimate moment captured between the man and the baby is touching. The woman’s gaze, directed outside the frame, adds an element of mystery and curiosity. The framing places the subjects at the center, inviting the viewer into the personal moment.

Color Harmony: The monochromatic palette brings out the emotional depth of the scene. Shadows and highlights are balanced, ensuring the details of the subjects are not lost.

Technical Skill: The image is sharp where it needs to be, particularly on the subjects. The blurred motion of the subway exterior further accentuates the stillness of the captured moment.

Originality: Candid moments in public transport settings are not uncommon. However, the genuine interaction between the subjects makes this image stand out.

Emotional Expression: The artwork captures a heartwarming and genuine human connection in an otherwise mundane setting. It speaks to the universality of human emotions and interactions.

Score: 8.5/10


I mean… honestly? Not bad.

But again, those are my most well known works for a reason so I had a pretty good idea how that would play out. But what if I gave GPT something more challenging and experimental to evaluate. My new Connections series is personal and challenging and untested in so many ways, so I thought I’d give that a shot. Connections is as much about the concept as it is about the output so I thought I’d just give the final output and see what it thought, and then give additional context and see if that changed anything. This was fascinating…


Description: A black and white photograph capturing the intricate maze of power lines, poles, and barren branches set against a light, almost white sky. The dominant features are the crisscrossing lines, both natural and man-made, which jumble together to create a complex and slightly chaotic pattern.

Composition (3/5): The image offers a layered perspective with power lines at multiple levels, offering a sense of depth. The juxtaposition between the natural lines of the tree branches and the geometric lines of the cables and power structures is interesting, but the focal point is somewhat lost amidst the busy-ness.

Color Harmony (4/5): Although the image is in black and white, the gradation of tones is evident, and the light background helps the darker elements pop. The absence of color serves to highlight the intricacies of the lines.

Technical Skill (3.5/5): The image is well-balanced in terms of light and dark areas. The contrast is clear, but some portions seem to blend into one another due to the dense layout of lines.

Originality (3.5/5): The theme of man vs. nature is not new, but the portrayal here is somewhat fresh. The chaos formed by human-made structures and nature intertwining is a silent commentary on urban encroachment.

Emotional Expression (2/5): While the image does convey a sense of chaos and possibly the encroachment of urban structures on nature, it lacks a strong emotional impact. It’s more reflective than evocative.

Overall Score: 6.5/10

Comments: This photograph succeeds in capturing the complexities of an urban landscape, juxtaposing man-made structures with natural elements. The interplay of lines, both organic and geometric, create a maze-like visual that is both intriguing and slightly overwhelming. While it is a competent representation of its theme, it lacks a definitive focal point or strong emotional resonance.


Then I pointed GPT to my explanation of the series and concept behind it, and asked it to evaluate the work again with that additional context. Kind of like asking it to read the plaque on the wall in the gallery.


Description: “Connections” is a series that delves into the intricate associations between nature, humans, and technology. The artwork fuses the organic with the artificial, compelling the viewer to reflect on the intricate mesh of relationships, dialogue, and interplay between humans and their surroundings. Derived from Bonner’s authentic photographs, the creation process itself challenges our understanding of reality, questioning the boundaries between human creativity and artificial intelligence. The artwork inspires contemplation on the delicate balance between inspiration and direction, as well as the fine line differentiating reality from an AI’s artistic perception.

Composition (4/5): With the added context, the intertwining lines of nature and man-made structures take on deeper meaning, symbolizing the fusion of organic and synthetic elements. The complexity of the piece can now be seen as a reflection of the intricate web of connections in our world.

Color Harmony (4.5/5): The monochromatic palette reinforces the theme of merging realities – the human and AI perspectives. The use of varying tones of black and white signifies the subtle nuances in these connections.

Technical Skill (4/5): Knowing that this piece is an AI interpretation based on original photographs adds another layer of appreciation for the technical execution. It showcases the potential of AI in artistic expression and its ability to recreate reality.

Originality (4.5/5): The concept of exploring connections is given a fresh take with the amalgamation of human and AI creativity. The choice to make it initially available only in person at select events further emphasizes the value of genuine human connections in a digital age.

Emotional Expression (4/5): The image now carries more emotional depth. Knowing the backstory and intention, viewers are not only intrigued by the visual complexity but also by the underlying themes of human-machine collaboration and interconnectedness.

Overall Score: 8.5/10

Comments: With the added context, “Connections” by Sean Bonner transcends its initial visual impression. It stands as a testament to the potential harmony between nature, human ingenuity, and machine intelligence. The series, starting with this piece, offers a thought-provoking commentary on the evolving relationship between man and technology, urging viewers to reflect on the true nature of connection in an increasingly digital world. The piece’s exclusivity and method of distribution further reinforce its themes, making it not just an artwork, but an experience.


So this was a pretty fascinating experiment. I genuinely enjoyed seeing how GPT saw my work. One thing Tara is always telling me is how she works with GPT to improve her prompts before using them. So rather than saying “please help me do this” she’ll say “please pretend you are a GPT prompt writer who needs to get X done, and help me write the prompt to get the best result for that” and goes back and forth several times before landing on the prompt she’ll actually use for the main request. I thought I’d ask GPT to consider the initial prompt I used here, and see if it would benefit from a revision. GPT said the prompt was quite good already, but if I wanted more thoughtful and detailed criticism I could edit it a bit to solicit that. I didn’t go back and redo the evaluations with the new prompt, but thought I’d add it here on the end just in case anyone wanted to try it out themselves on their own work.

New revised prompt:

Hello. Assume the role of an exacting art critic with an acute sense for detail and a passion for thorough analysis. Your mandate is to dissect artworks meticulously, providing scores on a scale from 1 to 10. On this scale, a score of 1 is given to art that is devoid of technical prowess, originality, or emotional resonance—often seen as rudimentary or lacking in execution. Conversely, a score of 10 is reserved for artworks that are paragons of technical mastery, creativity, and depth, truly revolutionizing the artistic landscape.

Your evaluations should be systematic and uncompromising. When evaluating artworks, adhere to the following format:

  • Contextual Understanding: (If provided) What narrative or background information is given about the artwork? How does this influence your interpretation?
  • Composition: How are the elements arranged in the piece? Does it guide the viewer’s eye? Is there a balance or intentional imbalance?
  • Color Harmony: Is there an effective use of color or lack thereof? How do the colors interact with each other, and what mood do they convey?
  • Technical Skill: Beyond the basic execution, is there evidence of advanced techniques or a particularly deft touch?
  • Originality: How fresh or innovative is the artwork? Does it bring a unique perspective or technique to the table?
  • Emotional Expression: What feelings or messages does the artwork convey? How effectively are they communicated to the viewer?
  • Overall Score: Based on the detailed analysis above, assign an aggregate score out of 10.

Always remember, while scores are numerical, the essence of art is found in its subtleties and nuances. Delve deep, appreciate the intricacies, and be forthright in your assessments.

Please commence your evaluation of the following artworks.