Teaching contemporary art can feel daunting—but it doesn’t have to be. One simple and engaging approach is to connect the artists already in your curriculum with living artists working today. This strategy helps students recognize how art evolves while maintaining ties to the past. It also encourages them to see how themes, techniques, and cultural influences transform across generations.

A great way to explore these relationships is through comparison activities like class discussions, writing prompts, or Venn diagrams. Whether in-person or remote, this method deepens understanding and makes art history relevant to students’ lives.
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Here are five artist pairings that bridge classic and contemporary art while inspiring classroom creativity:

​Pairing Kehinde Wiley’s After Titian’s “The Penitent Mary Magdalen” (2009) with Titian’s original (1555–1565) highlights how artists borrow from history. Both works share similar poses, yet Wiley updates the subject with a male figure in modern clothing against a patterned background. After analysis, have students create portraits that merge Renaissance-style poses with contemporary fashion or digital backdrops.

​When teaching Picasso’s Blue Period, compare it with Lisa Brice’s expressive, blue-toned paintings inspired by her experiences in South Africa and Trinidad. While Picasso used blue to convey melancholy, Brice’s use of the color connects to cultural celebration. Encourage students to paint or draw in a monochromatic palette that expresses an emotion or story of their own.

​Check out my Lisa Brice-inspired activity, here.

​Norman Rockwell captured pivotal ts—just as Kadir Nelson’s New Yorker cover honoring George Floyd reflects today’s social climate. Students can explore how both artists use realism to document and comment on history, then design their own magazine covers or illustrations addressing issues that matter to them.

​Keith Haring developed a universal visual language through bold, symbolic imagery. Contemporary artist Peat “Eyez” Wollaeger continues this tradition with his signature eye motif in street art and merchandise. Students can analyze their shared approach to accessible public art, then create their own personal symbols or “visual brands” to apply to prints, stickers, or apparel designs.

​Andy Warhol turned celebrity culture into fine art through colorful screenprints. Victoria Villasana reimagines that tradition by embroidering vivid thread onto portraits of icons like Frida Kahlo and Rihanna. Have students transform digital or printed celebrity images with mixed media, adding color, texture, and personality to make them their own.
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Final Thoughts

Comparing classic and contemporary artists invites students to think critically about visual language, style, and meaning. These pairings show that art isn’t static—it’s a living dialogue across time. By weaving in modern voices, you’ll not only enrich your curriculum but also help students see themselves as part of art’s ongoing story.

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Which artist pairings inspire you most?
What contemporary artists are you excited to bring into your classroom next?

Social-Emotional Learning (SEL) has become a cornerstone of education. Art educators have always understood why. The art room is a natural space for students to explore who they are, reflect on what they value, and make sense of the world around them.
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Reading Sara K. Ahmed’s Being the Change: Lessons and Strategies to Teach Social Comprehension reaffirmed this belief for me. Ahmed defines social comprehension as helping students make sense of themselves and others through awareness, empathy, and inquiry. Her ideas translate seamlessly into art education, where creative expression and reflection already go hand in hand.

Identity: Who Am I?
Every project in the art room is, at its core, an act of self-expression. When students create self-portraits, design symbols that represent their values, or collage elements of their personality, they’re not just making art—they’re defining identity.

As they share their work, they begin to recognize shared experiences and differences. A student might notice that a classmate used the same word, “gamer,” “musician,” or “athlete” in their project. These small moments build empathy and remind us that the art room is a community, not just individual students.
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When we make students’ thinking visible and encourage empathy, we build trust in the classroom.

Bias: Seeing with New Eyes
Ahmed reminds us that bias is “when we have our mind made up about something based on a prior experience, our environment, or some part of our identity.” It’s a universal human tendency—but also an opportunity for reflection.

One activity I’ve tried is facilitating class discussions on the work of artist, Kehinde Wiley. We begin by watching a Today Show interview where the artist speaks about his work, and how it encourages the viewer to question how race and social power influence art. Students compare and contrast Wiley's work with the European portraits they were inspired by. This gentle exercise helps them see their own assumptions without judgment.

From there, we discuss bias in the art world itself: Why do so many textbooks focus on male, European artists? Whose voices are missing? These questions help students challenge the visual narratives they’ve inherited.

Check out my Green Screen Photo Portraits unit plan, inspired by Kehinde Wiley, here.

Awareness and Empathy: Making Meaning
SEL also helps students understand how their identity shapes what they notice and value. I often ask them to share what’s “newsworthy” in their own lives—a birthday, a team win, a new sibling—and then express that moment visually.
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As they illustrate their “news,” students begin connecting their experiences to larger themes. They see how personal stories become universal and how empathy grows through art.

Inquiry: Asking Better Questions
Once students start reflecting on identity and bias, curiosity naturally follows. They begin asking: What don’t I know? What can I learn from others?
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Encouraging them to research new artists, explore diverse cultures, or challenge stereotypes transforms art from simple creation into inquiry. This process empowers students to use art as a tool for understanding and change.

The Art Room as a Mirror
Teaching social comprehension through art helps students see beyond the surface—to recognize their biases, empathize with others, and understand their role in the broader world.

Art educators don’t just teach technique, we teach reflection. We invite students to explore the world within themselves and beyond. In these moments, we see students creativity and compassion grow in the art room each and every day.