DALLAS, TX.- The two most effective and recognizable political images in our lifetime came from a guerilla street artist-turned-pop-art wizard named Shepard Fairey. His first was conceived in 1989, when he was 19, and ultimately became the ubiquitous “Obey” picture that features the screen-printed and abstracted face of Andre the Giant and the all-caps directive OBEY — Fairey’s Orwell-inspired jab at collective conformity. He unleashed upon the world his other most famous artwork during the 2008 presidential campaign of Barack Obama — the original of which is being offered by Heritage on May 14 in its Modern & Contemporary Art Signature® Auction. In 2008, the then-unauthorized picture was adopted by the Obama campaign as its official logo. A year after his Obama HOPE picture went viral and solidified Fairey’s reputation as one of the world’s most reproduced artists, and upon an early-career retrospective of his work at Boston’s I.C.A., the New Yorker’s indomitable art critic Peter Schjeldahl wrote of the artwork:

“The reward with Fairey’s picture was a thrill of concerted purpose, guarded against fatuity by coolly candid deliberation. The effect is that of epic poetry in an everyday tongue.”

The R.I.S.D.-degreed Fairey is to this day (Bansky notwithstanding) arguably the art world’s most popular populist artist — he is in other words most prominent artist since Andy Warhol to introduce a smart conceptual art form into the general lexicon of art itself, and like Warhol, he did it by combining a genius mix of five crucial elements: the mimetic power of advertising vernacular, proven propagandistic visual strategy, sophisticated graphic design, aspirational imagery … and killer timing. And despite the image being now so iconic and reproduced that it seems part of the very air we breathe, there are, in fact, only three 2008 Fairey handmade originals of HOPE (Barack Obama) in existence: One of these canny, beautiful and monumental collage-and-stencil originals was acquired by the National Portrait Gallery in Washington D.C. even before Obama’s inauguration (a first for the NPG); another is in a private collection. The original offered by Heritage, which leads an event featuring significant works by national and international artists, comes to auction in this tumultuous election year and boasts the gravity of extreme hindsight. Writes Schjeldahl: “Fairey’s splendid tour de force for Obama anticipated a new national mood, of serious-minded pragmatism, which makes ideological extremes seem sort of quaint.” That the original is being made available to the public now feels momentous.

“We are honored to offer this important work at auction — this image defined an entire movement and Barack Obama's presidency,” says Taylor Curry, Heritage’s Director of Modern & Contemporary Art in New York. “It is one of only three large-scale HOPE works made by Shepard Fairey in 2008; one resides in the National Gallery at the Smithsonian, and another is held in a private collection.”

For HOPE (Barack Obama), Fairey lifted the image of the future president from an Associated Press photo taken by Mannie Garcia; Fairey then built up on paper a background of, as Schjeldahl puts it, “wallpaperlike patterns or fragments of newspaper pages, which impart a palimpsestic texture and a flavor of antiquity,” and then overlays it with stencil and acrylic graphic abstraction of the instantly-recognizable Obama and the single, telling word HOPE. The work is signed and dated center left: Shepard Fairey 08. And thus a true American icon of a true American icon was born. As Schjeldahl put it, “Fairey created the most efficacious American political illustration since ‘Uncle Sam Wants You’ … In innumerable variants, the craning, intent, elegant mien of the candidate engulfed the planet.” This feels like a lifetime ago as much as it feels like yesterday. This is what a great artwork can do.

Regarding other highlights in this May 14 auction, we now jump from the United States to other times, moods and continents. When Fernando Botero died last year, he left behind his legacy as the greatest of all Colombian artists, if not the most popular of all Latin American artists. His distinctive style, eventually coined "Boterismo," presents his figures in voluminous, inflated form; they are instantly recognizable (and beloved) the world over. One lead in this auction is an emblematic marble by the artist: Caballo is a Botero horse that showcases the artist's playful eye for the hoofed animal's healthy proportions; it is generous yet intimate and “Boterismo” through and through.

Italian sculptor Arnaldo Pomodoro originally studied architecture, and his work reflects the engineering and formal impulses and concerns of his architecture peers, as well as that of avant-gardists Lucio Fontana and those of the Spatialist movement. His large bronze study for his monumental Grande Portale Marco Polo, the largest work exhibited at the 2010 Shanghai World Expo, is offered in this event, and it proves Pomodoro’s gift for using abstract geometric forms to push and pull within and without the frontal planes of the bronze doors. The biomorphic points of punctuation lend a remarkable fluidity to the material that translates across major changes in scale.

On the topic of architecture meeting art, we cross the pond back to the U.S. and the unique conceptual brilliance of Gordon Matta-Clark, also a student of architecture and then a central and organizing figure of the 1970s downtown New York art scene. David Zwirner aptly describes him as pioneering “a radical approach to art making that directly engaged the urban environment and the communities within it, including large-scale architectural interventions in which he physically cut through buildings slated for demolition. His work transcended the genres of performance, conceptual, process, and land art, and made him one of the most innovative and influential artists of his generation.” On May 14 Heritage offers one of Matta-Clark’s crucial photographic works, the dye coupler prints Doors, Through and Through (or Doors, Floors, Doors) (triptych) from 1976. It’s his own documentation of his original intervention for the inaugural group exhibition at P.S.1, for which he cut door-shaped holes on three consecutive floors of the former school building; the cuts created the illusion of trap doors casting shadows.

Other highlights in this auction include a rolled steel Arc by French conceptual artist Bernar Venet. The unique 83.5° Arc x 8, from 2013, was designed as an indoor piece and epitomizes the artist’s curving and dynamic, if not mathematically precise, sculptural work. Also included in the auction is a significant relief by the Brazilian-born, Argentinian- and French-trainedSérgio Camargo, an artist who synthesized conceptual art, Neo-Concretism and Constructivism in his work. Relief No. 173, from the artist’s prime in 1967, is a painted wood construction that juxtaposes smoothness and texture.

“Here Camargo invites the viewer to participate in the act of artistic creation,” says Curry. “It prompts them to discern order and coherence within the dynamic interplay of light and substance, both within the relief's intermingling of shadows and within the very essence of the wood itself. This remarkable example of Camargo’s output is but one of 75 distinctive works on offer at Heritage on May 14.”

Says Frank Hettig, Heritage’s Vice President of Modern & Contemporary Art, “This small and exquisite auction will emphasize the best representation of national and internationally important artists, emphasizing Heritage’s dedication to showing important and unique works. We are connecting art history, including Surrealism and figurative works, with significant present-related artworks.”

Indeed, these are the artists who have shaped our culture’s very idea of what art can be and the role it plays in our aesthetic, intellectual, and political lives.