Bridging Classic and Contemporary Art

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:

1. Kehinde Wiley and Titian

​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.

Check out my Kehinde Wiley-inspired lesson plan, here.

2. Lisa Brice and Pablo Picasso

​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.

3. Kadir Nelson and Norman Rockwell

​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.

4. Eyez and Keith Haring

​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.

5. Victoria Villasana and Andy Warhol

​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?