When Elspeth Michaels ’05 submitted her newsletter proposal for the inaugural Joel Gay Creative Fellowship, the odds were stacked against her. The fellowship, which was founded by New York Times bestselling author Roxane Gay and supports emerging writers, was offered to just three applicants selected from a pool of over 1,500.

Impressively, Michaels was one of those three, and she’s since gone on to launch The Drip, a weekly newsletter on the Substack platform that explores the intersection between art history and hip-hop.

“[The Drip] is where the mixtape meets the sketchbook,” Michaels explains. “Each month, I take a concept and break it down through weekly essays. My goal is to create an accessible space for art history and hip-hop to collide.”

Michaels says the idea started percolating during college at the University of Chicago, where she was an art history and visual arts major. “One day in my photography class, my professor said, ‘Art history is one big inside joke.’ To exist in the canon, he implied, artists make their place by studying and referring to the greats. Something clicked for me at that moment. The more I learned about art, the more I started making these deeper connections.”

At the time, Michaels was listening to Kanye West, Common, and Lupe Fiasco as they came into fame and collaborated on albums that told stories about Chicago’s South Side. Her understanding of lyrical connection to place, culture, and memory gelled in new ways as she was also honing a more academic framework through which to analyze art.

“Both hip-hop and art history share a self-referential practice,” she notes. “The more you listen and look, the more you start connecting samples and styles, bars and brushstrokes.”

Reflecting on her youth, Michaels says that she would listen to music while drawing, and has always been inspired by the ways the two connect. Her passion for art really flourished while taking classes at Taft.

“Some of my fondest memories from Taft were listening to albums in the art studio while painting with friends and singing in Hydrox,” she recalls. “I thought about this connection [between music and art] for over a decade and knew I wanted to do a project about it, but I wasn’t sure what form it would take.”

Michaels’ career path—and her journey to creating The Drip—was anything but linear. After college, she moved to Japan where she taught English for two years.

“I knew I wanted to pursue a career in the arts,” she says. “But I also wanted to travel and experience my own culture as an adult, having moved to the U.S. when I was three. [Going back and] teaching in Japan was an incredibly meaningful experience for me.”

When Michaels returned to the States, she freelanced in San Francisco before completing a certificate program in graphic design at UC Berkeley Extension. She then moved to New York, where she enrolled in a user experience design program at the Pratt Institute and fully committed to a career in both design and writing.

In 2020, Michaels received the exciting opportunity to return to Taft to teach part time. “I’d been so focused on becoming a designer, and this brought me back to my love of art and back to the classroom, where I was mentored by my former teachers Loueta Chickadaunce, Bruce Fifer, and Steve Palmer.”

For Michaels, teaching at Taft was the initial catalyst for The Drip.

“I missed the creative process of building a curriculum and sharing ideas within the community of a classroom,” she says. “So I decided to write a newsletter, replicating the process of research, building off concepts, and distilling them into mini-lessons.”

In December 2021, she launched a prototype of The Drip. In February, a friend forwarded her Roxane Gay’s call for submissions, and she applied for the fellowship on a whim. A month later, she received the incredible news that she’d won.

“I fully expected a rejection or no response at all,” Michaels admits. “It’s been almost six months now, and I still can’t believe it.”

Michaels, who also works as a graphic/UX designer at Mass. General Hospital, hopes that The Drip will be a launchpad for a book about how different art forms interconnect. Clearly, she’s onto something.