New York–Swann Galleries’ annual Graphic Design sale on Thursday, May 23 features important designers, such as Adolphe Mouron Cassandre, Charles Loupot and Tadanori Yokoo. On display is the evolution of design in the last century, from exceptional Constructivist images of the 1910s, to Psychedelic Rock-and-Roll posters and corporate propaganda from the 2010s.

            A spectacular run of luxury advertisements by Parisian postermaker Charles Loupot leads the sale. Highlights include a 1930 poster for Twining Tea and Lion Noir / Cirage – Crème, 1949, which features a black lion preparing to pounce ($30,000-$40,000 apiece), a dizzying 1926 ad for the French automobile company Peugeot ($40,000-$60,000), and Wanneroil / Huile du bon Chauffeur, 1926 ($20,000-30,000).

            A.M. Cassandre is present with his revolutionary 1927 travel poster, Étoile du Nord, offered at $15,000 to $20,000. The advertisement features no landscape, no destination and no train, a startlingly new concept for the time. Additional works by Cassandre include Nederlandsche Nyverheidsten Toonstelling / Rotterdam, 1927, and Triplex, 1931 ($8,000-12,000 and $20,000-30,000, respectively).

            Italian Futurist posters include the only “free word” typographic poster from the era, Futurismo, 1932, by Filippo Tommaso Marinetti and Lamberto Leandri ($12,000-18,000). The poster appeared as a folded insert in issue 29 of the short-lived newspaper of the same name. Also of note is Giacomo Balla’s 1933 notice for an exhibition of Umberto Boccioni’s works presented by the Congresso Futurista Italiano ($3,000-4,000).

            Constructivist highlights include Create the “Week of the Red Gift” Everywhere, 1919, by Wladyslaw Strzeminski ($40,000-60,000)–the 13th poster produced by Litizdat, the poster arm of the Political Directorate of the Revolutionary Military Council of Russia, and potentially the inspiration for Lissitzky’s Beat the Whites with the Red Wedge. Strzeminski’s The Organization of Production is Victory Over the Capitalist System, circa 1919, also features at $40,000 to $60,000.

            A wave of Japanese artist Tadanori Yokoo’s late-1960s psychedelic posters is set to come across the block with Having Reached a Climax at the Age of 29, I was Dead, 1965, leading the run at $20,000 to $30,000. Other notable lots include Yukio Mishima / The Aesthetics of End, 1966, estimated at $10,000 to $15,000, Laboratory of Play / Tenjo Sajiki Troupe, 1967, and Takarazuka / Grand Revue, 1966, poised to sell for $8,000 to $12,000 each.

            Bonnie MacLean, Martin Sharp and Wes Wilson star in a selection of psychedelic Rock-and-Roll posters: a group of seven of MacLean’s designs promoting the likes of Steve Miller Band and Pink Floyd carries an estimate of $1,000 to $1,500; a 1967 poster for Cream by Sharp is present at $800 to $1,200; and Wes Wilson’s The Association / Filmore Auditorum, 1966, is expected to bring $1,500 to $2,000.

            Paul Rand’s transformative designs include his cutting-edge 1982 image for IBM ($2,000-3,000). A group of 13 Facebook propaganda posters, by various artists from 2010-14, broadcast messages like “kick the shit out of option B” and “nothing at Facebook is somebody else’s problem,” bringing the sale into the digital age ($1,500-2,000).

            Exhibition opening in New York City May 18. The complete catalogue and bidding information is available at swanngalleries.com and on the Swann Galleries App