When my family is going on a long road trip, I like to print out discussion questions to minimize screen time and torture my family. On our last trip, one of the questions was, “What is something you could talk about for thirty minutes straight, without any preparation?” My answer? The Enneagram. Whether you are brand new to the Enneagram, or a seasoned vet, my hope is you will find the descriptions below to be at least a little accurate. One of the awesome things about the Enneagram is that it takes into consideration how very onion-y humans are. I’m a Nine, but there are days I could be mistaken for a Three, moments you might swear I’m an Eight. People have layers! So, if the art or artist assigned to your number doesn’t resonate? No big deal! It’s art. You can like all of it or none of it. If the Enneagram teaches us anything, it’s how very complex we are. And your artistic tastes can be just as compound! What I’m trying to say here is: this is just for FUN!

If you don’t know what Enneagram number you are, there are approximately ten million quizzes online. Here is one. Have fun! Discuss with friends! I suggest taking it on a road trip for some good, old-fashioned torture conversation.

Enneagram 1 (The Reformer): If you won’t leave the house with a wrinkle in your dress, the dishes done, and every tissue box square with the table on which it sits? You may be a One. Ones are perfectionists, organizers, crusaders! You keep the cogs of society running. Recruit a One to pull off the best fundraiser the PTA has ever seen! Maybe they want to do an art drive. If so, Ones might be tempted to pick a lot of paintings from the Baroque period. They will appreciate the ornate details characteristic of Baroque art. The Baroque era began in response to a distaste for simpler art- a reformation perhaps led by artistic Ones. Many Baroque paintings are inspired by history, making great tools Ones can use in their crusade to educate others. I recommend Ones check out works by Caravaggio and Rembrandt, but especially Vermeer.

Vermeer loved to paint quotidian tasks. He was an expert at making the ordinary look extraordinary. Reformers do this same thing, I think. They appreciate stability and find joy in a job well-done, whether it’s a painting or an everyday task.

Enneagram 2 (The Helper): Twos are irresistible. They are generous and compassionate and make great friends. I can vouch for that- some of my best friends are Twos. My best guess is that these Helpers really enjoy Installation art. For one thing, lots of Installation art is also interactive, so Twos can bring a friend along to share in it. Installation art sends a big message to viewers. It is almost always found in a large space and is hard to miss. Twos send a big message as well- in how they interact with the world through their generosity and support. Installation art is a fairly new artistic genre. The Twos in your life may love discovering some of Carsten-Holler’s bright, funky work, or Olafur Eliasson’s trippy installations. The artist whose work I think will resonate with Twos best is Doris Salcedo.

Like much art, this work comes from a place of sadness. But Twos can handle sadness. They want to feel connected to people and the story behind this installment will accomplish that. Helpers have a knack for seeing people for who they really are… I bet they’re equally good at interpreting art.

Enneagram 3 (The Achiever): It’s hard not to admire the Threes in our lives. They are so inspirational and motivating! Threes put a lot of value on succeeding, whatever that means for them (it’s not necessarily financial.) Whether it’s getting an academic achievement award, completing an Iron Man, or making their first million, Threes make goals and achieve them. I think they may find themselves attracted to the art form known as Fauvism. Fauvism was a short-lived movement in Paris, but its influence rippled through the art world for years. Like Threes, it was influential and authentic. A new art form for its time, Fauvism served as a model (as Threes often do!) to subsequent art forms. Threes may be attracted to art by Gustave Moreau or Andre Derain, but Henri Mattise was the most successful of all Fauvism artists.

Le Bonheur de Vivre is considered the greatest painting in Fauvism, and I know Threes appreciate the greatest of anything! This painting is almost 6 feet high and 8 feet wide- it’s very “go big or go home.” Just like our beloved Threes!

Enneagram 4 (The Creative): As the rarest of all Enneagram numbers, it would be easy to assume Fours would be into a unique art form, like Intentism or Fluxus. Sometimes Fours are known for their comfort with melancholy, so we might guess they’d be into Picasso’s blue period. But actually, the kind of art I think Fours might be most attracted to is Surrealism. Fours are creative, they’re dreamers! And Surrealism is all about painting trippy scenes we may only see in a dream. Think Salvador Dali’s “The Persistence of Memory” or “The Two Fridas” by Frida Kahlo. I think the painting that best embodies a Four is one of my favorites: “Over the Town” by Marc Chagall.

It is lovely and romantic, but this couple has a sad ending: it is a self-portrait of the artist with his wife, Bella, who died unexpectedly. Chagall grieved her for years, unable to work. I think the unique scene, sad backstory, and romance of this painting is very “Four-esque.”

Enneagram 5 (The Investigator): I really, really wanted to keep the Renaissance for Nines because it’s my favorite era, but if I’m being honest… I have to give it to the Fives. Renaissance paintings have elaborate stories behind them to dig into, and details for Fives to take a bite out of and savor. And when they’re done digesting the symbolism behind say, Thomas’ index finger in The Last Supper, there’s another detail to consider. Perhaps the table salt. Fives could really sink they’re teeth into paintings like The Last Judgement and Ecstasy of Saint Francis. But the one that will really set their minds reeling, that you may never be able to tear them away from? I think it’s Raphael’s The School of Athens.

Do you know a Five who would love to study each character in this painting and their backstory? It features Plato and Aristotle (were they fellow Fives? Good chance!), math books, architecture… it’s a virtual playground for our investigative, observant Fives!

Enneagram 6 (The Loyalist): Enneagram experts think there may be more Sixes in the world than any other number. What a comfort! I love knowing I could be surrounded by a loyal, prepared, ready-for-anything Six at any given time. The art style I think best represents Sixes is Impressionism. When Monet first introduced the technique to the world, there was some real push-back, but Impressionists believed in the art form and persevered, the same way Sixes do when they believe in something. Sixes strive to find peace even in the chaos of life, and doesn’t Impressionism do the same? The most famous paintings in this genre are haystacks, ponds, ballerinas, all painted in soothing strokes. Sixes may find themselves absorbed in the works of Edgar Degas or the father of Impressionism, Claude Monet. But I think they may especially love Mary Cassatt’s paintings.

Cassatt loved painting mothers and their children, and isn’t that relationship the epitome of loyalty? Sixes will find comfort in Cassatt’s calm paintings. But though they are calming they are still fun, never boring. A lot like many Sixes I know!

Enneagram 7 (The Enthusiast): Everyone loves a Seven! If Sixes are loyal golden retrievers, Sevens have the boundless energy of border collies. Sevens are exclamation points! They’re pogo sticks! They ride roller coasters with their hands up! If your little brother is a Seven you probably got a lot of wet willies growing up. They always have a project going, often several at once (sidebar: my husband is a Seven.) Sevens are fun and energetic. They are very similar to the art of Pointillism. Tiny little dots of energy making one beautiful masterpiece- just how Sevens are made! Van Gogh dabbled in Pointillism, and Paul Signac did some beautiful paintings that might resonate with you. But the master of Pointillism, of course, is Georges Seurat.

Did you think I was going to showcase Seurat’s more famous painting, A Sunday Afternoon on the Island of Grand Jatte? Nope! This is unexpected- like Sevens can be! These models are enjoying life, just as our dear Sevens are wont to do.

Enneagram 8 (The Challenger): Eights might have the nickname “Challenger,” but they’re also famously good leaders, protectors, and entrepreneurs. When I want an honest opinion, I go straight to an Eight. They will not sugarcoat the truth, which I appreciate, but are still polite and kind about it, which I appreciate even more. During a crisis, you want an Eight on your side. On your wedding day you REALLY want an Eight on your side. They are making sure nobody else wearing a white dress steps foot in the church, and that the DJ plays “Don’t Stop Believin’” on the hour. Eights are keeping it real, and it shows in their art preferences. You might find them admiring Rodin’s The Thinker or Edward Hopper’s Nighthawks, but they might like Van Gogh’s The Skull of a Skeleton With Burning Cigarette best.

Our Challengers will appreciate the blunt subject matter in this painting. Moms who are Eights will wave this in front of their kids faces, exclaiming, “this is what happens when you smoke!” Van Gogh took an anatomy class to get the details of this skeleton just right, and Eights appreciate that accuracy and no-nonsense style of learning.

Enneagram 9 (The Peacemaker): I felt morally obligated to give the Investigators the Renaissance, but I know you Nines won’t fight me on it (haha). The good news is Peacemakers like us are most likely to resonate with another beautiful art form: Expressionism. Expressionists take a situation and alter it to evoke particular moods or emotions. Raise your hand if you are a Nine who does the same thing. Expressionistic paintings aren’t literal interpretations of what the artist sees and Peacemakers aren’t always “what you see is what you get.” Van Gogh did plenty of Expressionism, and Edvard Munch became quite famous from his Expressionistic painting, The Scream. I think the artist that best captures the Peacemakers’ “Nineness” is Wassily Kandinsky.

Nines are at the top of the Enneagram circle. We can see (and embody!) the good and not-so-good characteristics of all the numbers in their beautiful cacophony. Kandinsky’s Composition VIII tells the story of a day in the life of a Nine: harmony, discord, straight edges, curves, bold colors and pastels. Nines make it all work together, as Kandinsky did in this painting.