Remembering Buddy Esquire, the King of the Hip-Hop Flyer

Illustration by Nick Gazin

I first met Buddy Esquire last August, when I was grazing through Afrika Bambaataa's record collection. Johan Kugelberg had been publicly archiving the 40,000 records, and he let me DJ them as a birthday present. At first, I felt like nothing could top DJing the copy of Trans-Europe Express that Bambaataa sampled for "Planet Rock," but then Johan introduced me to Buddy, the "Flyer King."

He was wearing a classic flyer T-shirt, so I assumed he was cashing in on some clothing deal from the birth of hip-hop. It turned out that his shirt was one of a kind. He’d been putting his own art onto clothing for a long time, because it was his way of getting exposure. He painted anime characters onto the shirts back in the 80s, long before anyone thought to translate them. But he was broke.

A Buddy Esquire book was in the works, with Johan, the maven that he is, as the publisher. Johan suggested I interview Buddy since we were both into flyers and comics. After the first interview, I just had to spend more time with Buddy. I interviewed him a total of three times.

Buddy was a self-taught artist. His style was all Art Deco and mostly looked like jukeboxes and classic theater marquees. His work brought life to the music he was advertising, with his abstract shapes and patterns. Although Buddy's work is associated with music, he told me that he rarely went to any of the jams he made flyers for. He was a homebody. A meticulous worker.

Buddy held himself to an overly-critical standard, always struggling to reach perfection. I often thought Buddy’s work was perfect, but I understood his need to constantly self-improve. An artist doesn’t achieve what Buddy achieved with contentment. Even when Buddy tagged my sketchbook he apologized. I had to reassure him it was good. And it was good.

My interviews with Buddy were pretty intense. Although he didn’t often go into details, it was clear that a lot of people had hurt him in his life. Buddy kept drawing, but his career took a severe dip when the old-school hip-hop scene ended. He made all these great images and was an integral part of the birth of something great, yet he worked for UPS and didn't have a bank account.

When Johan texted me to tell me Buddy had passed, I first misread it as “a buddy” had died. I had to reread it three times to understand which buddy of Johan's was dead before it sunk in. Maybe that's denial, or maybe I’m just stupid.

When I think of Buddy's death, I feel like a wave of depression and disappointment are washing over me. Buddy died at 58, which is tragic. I always fantasized that the Buddy Esquire book would reignite his career and he could do art full-time. I am very grateful that I got to talk to Buddy at length about his art. I know that eventually, when the Buddy Esquire book gets released, the world will finally know him. But it's killing me inside that Buddy won't get to witness it.

—Nicholas Gazin

Hip-hop in its infancy had no media traction. Years passed before anyone paid attention, except for the community itself—first generation hip-hop performers could draw four-figure audiences in the Bronx back then. Hip-hop began as a performance-based culture. It was based on live performance, based on showmanship from the DJ and the MC, and based on Saturday night. By the time the first hip-hop record was issued (early 1979, but scholars and Wallys still argue about which was first), the culture had been booming for at least six years.

Buddy started writing graffiti in 1972. He tagged and collected the tags of others in black books while steadily advancing his craft as a draftsman. He designed his first flyer in the summer of 1977, for a neighborhood block party. His first flyer for a hip-hop jam arrived a year later. Buddy started making flyers on the heels of the artist Phase 2. The two of them created elaborate designs for live hip-hop performances several times a week. The flyers became a matter of prestige for the artists and the promoters—having a flyer designed by Buddy Esquire became a standard for promoting a live hip-hop event.

His work combined stark, chiaroscuro shapes with a joyful tension between letters, photos, and ornaments. Cameras were a rarity in the Bronx, so the few photographs that existed were recycled from flyer to flyer. It's still exciting to trace the visual influences of the designs: Clear, arresting surfaces of visual virtuosity were inspired by Marvel Comics, by Star Wars, by boxing posters, by disco record sleeve graphics, by the facades of the Art Deco movie palaces that still existed in a crumbling state in the 1970s Bronx. Buddy Esquire incorporated all these elements into his timeless designs. His evolution as an artist—from his early work with traced letters and Vaughn Bode–style flourishes to his early 80s masterpieces of stark Bronx/Star Wars deco—is clear.

I had the privilege of working with Buddy for more than ten years, archiving his work for Cornell University and including it in the book and traveling exhibit Born in the Bronx. Buddy was kind and patient when younger artists and hip-hop fans came up to him. He was always gracious with his time and knowledge.

Buddy Esquire designed hundreds of flyers from 1978 on, but he never made a living from his art—instead working at UPS for several decades. Sometimes fame and fortune doesn’t come to the people who were there first. Buddy truly knew the value and influence of his work. He never showed bitterness over his level of fame and recognition. He told me that he was proud of his art, and that he felt that its influence would continue on for a long time.

Here’s a great interview with Buddy Esquire.

—Johan Kugelberg

The funeral for Buddy "Esquire" Thompson will be held at McCall's Bronxwood Funeral Home in the Bronx, NYC, on Saturday at 9:30 AM.