Goyita" (1953), one of Rafael Tufiño's best-known works.
Tufiño, whose prolific work includes paintings, drawings, prints and posters, died at a San Juan hospital.
The loss resonated deeply in New York, where Tufiño - known as "The People's Painter" was born and lived as an adult.
"He was a legend of our time," said New York-based artist Miguel Luciano. "He really represents el corazón de Puerto Rico [the heart of Puerto Rico]."
In 2003, Tufiño received a Lifetime Achievement Award from the National Arts Club in Gramercy Park - the first Puerto Rican to receive such distinction.
That same year, El Museo del Barrio in New York showcased a wide-ranging retrospective on 65 years of his work.
Among his best-known works are the paintings "El cortador de caña," (Cane Cutter) and "La Goyita," which depicted the island's impoverished rural class.
Born in Brooklyn in 1922, Tufiño was raised in Puerto Rico and then went on to live in Mexico and back in New York.
"He was very influential," said Marcos Dimas, 63, founding member of the East Harlem-based non-profit arts organization Taller Boricua, which Tufiño helped create in 1970.
Dimas, who has known him for 49 years, said "El Tefo" - as his friends would call him - transmitted his "technical skills and artistic accomplishments" to younger artists.
"Also, he was a link between New York Puerto Ricans and the artists from the island," he added.
Dimas says in the '60s they lived and worked on a building at 110th St. and Madison Ave., across the street from where the Puerto Rican nationalist group Young Lords was based.
"We did a lot of the poster work for the movement of the Young Lords," he said.
"Tufiño's emphasis was on using art as an education and advocacy tool to promote self identity."
Many years later, the artist would also inspire the much younger Luciano, 36, who was born in Puerto Rico but grew up in the U.S.
"My Puerto Rican art history, I had to learn on my own," Luciano said. "And his carteles [Posters] from the 50s, his paintings … these where the ways that I connected with that history."
Luciano added, "He also represents the back and forth and the experience of Puerto Ricans in both places."
Tufiño, who was married twice, is survived by five adult children.