For ‘American Cool,’ the National Portrait Gallery rounds up 100 indelible images of coolness

Frank Sinatra in 1956. (Herman Leonard, Institute of Jazz Studies, Rutgers University)

Frank Sinatra in 1956. (Herman Leonard, Institute of Jazz Studies, Rutgers University)

Ah, the good old USA. Land of the free and home of the cool.

“The coolest people live in America,” says Joel Dinerstein, co-curator of “American Cool,” a new exhibition at the National Portrait Gallery that celebrates 100 specimens of coolness. “The idea of ‘cool’ is central to the American self-concept. It embodies a characteristically American maverick individuality.”

“And pushing the boundaries of expression is a hallmark of U.S. democracy,” says Frank H. Goodyear III, the exhibition’s other curator.

“Cool” as we know it entered the American lexicon through African-American jazz musicians in the 1920s. Legend has it tenor saxophonist Lester Young popularized the word, throwing it around while playing shows. Later adopted by the mostly white members of the Beat Generation, the term eventually spread around the world. Today, if you say “cool” in almost any country, the locals will get what you mean.

Of course, not all people are created cool. Having studied the sociological history and meaning of “cool” since they were grad students at the University of Texas at Austin in the 1990s, Dinerstein and Goodyear devised a rubric of four “cool” characteristics, at least three of which must be met for a person to qualify. The co-curators looked for these attributes when picking subjects for their show: 1. An original artistic vision carried off with a signature style; 2. The embodiment of cultural rebellion or transgression for a given generation; 3. Iconic power, or instant visual recognition; and 4. A recognized cultural legacy.

Featuring photography by such masters as Diane Arbus, Henri Cartier-Bresson and Annie Leibovitz, “American Cool” presents portraits of the 100 people who best embody this truly American concept (a handful of whom were “cool” even before it was cool). Here are 10 standouts.

(Samuel Hollyer, National Portrait Gallery, Smithsonian Institution)

(Samuel Hollyer, National Portrait Gallery, Smithsonian Institution)

Walt Whitman (1819-1892)
By Samuel Hollyer, circa 1855

The father of free verse championed a radical new style of writing while challenging the prudishness of 19th-century society. The poet’s contemporaries were shocked and appalled by his non-rhyming verses, which audaciously explored “obscene” themes, including sexuality and homoeroticism.

Coolest Contribution: “Leaves of Grass,” 1855.

(Bob Willoughby, National Portrait Gallery, Smithsonian Institution)

(Bob Willoughby, National Portrait Gallery, Smithsonian Institution)

Billie Holiday (1915-1959)
By Bob Willoughby, 1951 (Printed 1991)

A friend of Lester Young’s, Lady Day often headlined at jazz shows but she still had to enter white clubs through the back door. Holiday’s heart-wrenching rendition of “Strange Fruit” exposed American racism like nothing else could: “Southern trees bear a strange fruit/ Blood on the leaves and blood at the root/ Black bodies swinging in the southern breeze/ Strange fruit hanging from the poplar trees.”

Coolest Contribution: “Lady Sings the Blues,” 1956.

(National Portrait Gallery, Smithsonian Institution)

(National Portrait Gallery, Smithsonian Institution)

Frederick Douglass (1818-1895)
By Unknown, 1856

Douglass fearlessly set out to prove that black slaves were as intelligent as their white masters and deserved to be recognized as independent human beings and American citizens. An escaped slave himself, the great orator fought for the equality of all people, regardless of race, gender or national origin.

Coolest Contribution: “Narrative of the Life of Frederick Douglass, an American Slave,” 1845.

(Roy Schatt, National Portrait Gallery, Smithsonian Institution)

(Roy Schatt, National Portrait Gallery, Smithsonian Institution)

James Dean (1931-1955)
By Roy Schatt, 1954

While Dinerstein and Goodyear were conducting preliminary interviews with anyone and everyone on the topic of “cool,” James Dean was one of two people who always came up first (Miles Davis was the other). A poster boy for disenfranchised youth, Dean literally lived life in the fast lane while breaking down boundaries in acting and sexuality.

Coolest Contribution: “Rebel Without a Cause,” 1955, one of only three feature films Dean made.

(Aram Avakian, National Portrait Gallery, Smithsonian Institution)

(Aram Avakian, National Portrait Gallery, Smithsonian Institution)

Miles Davis (1926-1991)
By Aram Avakian, 1955 (printed 2012)

Davis, whose 1957 album is even called “Birth of the Cool,” was most famous for pioneering a clear, vibrato-less tone on trumpet and being on the forefront of a handful of new jazz styles, most notably “cool jazz.”

Coolest Contribution: A tie between “Kind of Blue,” 1959, and “Bitches Brew,” 1970.

(Roger Marshutz, courtesy of Peter Marshutz and the Fahey/Klein Gallery, National Portrait Gallery, Smithsonian Institution)

(Roger Marshutz, courtesy of Peter Marshutz and the Fahey/Klein Gallery, National Portrait Gallery, Smithsonian Institution)

Elvis Presley (1935-1977)
By Roger Marshutz, 1956

Even the coolest of the cool bow down to Elvis. John Lennon considered the King such a huge influence that he liked to say, “Before Elvis, there was nothing.” Fellow “American Cool” subject Bob Dylan’s view: “When I first heard Elvis’ voice, I just knew that I wasn’t going to work for anybody, and nobody was going to be my boss. Hearing him for the first time was like busting out of jail.” Need we say more?

Coolest Contribution: “Elvis Presley,” 1956 (coolest album) and “Jailhouse Rock,” 1957 (coolest song and movie).

(Linda McCartney, National Portrait Gallery, Smithsonian Institution, Copyright by Paul McCartney)

(Linda McCartney, National Portrait Gallery, Smithsonian Institution, Copyright by Paul McCartney)

Jimi Hendrix (1942-1970)
By Linda McCartney, 1967

Hendrix, whose face graces the cover of the “American Cool” exhibition catalog, redefined the art of guitar playing — and even the sound of our national anthem. But his untimely death exposed a darker side of cool, a mysterious complexity that sometimes ends in tragedy for huge talents who don’t quite fit in. “Being ‘cool’ is often a strategy for navigating through a challenging society. It’s how you deal with the s— in life,” co-curator Joel Dinerstein says. “ ‘Cool’ is not [about being] heroic.”

Coolest Contribution: “Are You Experienced,” 1967.

(Julian Wasser, courtesy  of the Craig Krull Gallery, National Portrait Gallery, Smithsonian Institution)

(Julian Wasser, courtesy  of the Craig Krull Gallery, National Portrait Gallery, Smithsonian Institution)

Joan Didion (1934- )
By Julian Wasser, 1970

A firm believer in the sociocultural power of the media and a champion of literary journalism, Didion mapped new territory for writers. Using methods usually confined to fiction writing, she uncovered the ugliness behind the American Dream.

Coolest Contribution: “Slouching Towards Bethlehem,” 1968.

(Dmitri Kasterine, National Portrait Gallery, Smithsonian Institution)

(Dmitri Kasterine, National Portrait Gallery, Smithsonian Institution)

Jean-Michel Basquiat (1960-1988)
By Dmitri Kasterine, 1986

Often cited as one of the first true street artists, this Haitian-American Brooklynite helped usher graffiti (previously attributed to thugs and juvenile delinquents) into the art world. Basquiat would paint his signature three-pronged crown on his canvases and tag it on walls. To this day, street artists pay homage to their forefather by painting Basquiat’s crown into their own works.

Coolest Contribution: Tags that used to cover the walls and subway cars of New York City.

(Cass Bird, National Portrait Gallery, Smithsonian Institution)

(Cass Bird, National Portrait Gallery, Smithsonian Institution)

Benicio del Toro (1967- )
By Cass Bird, 2008

This Puerto Rican-born actor oozes cool, with his rugged masculinity, secretive private life and unwavering devotion to his art. In preparation for his 1998 role as Dr. Gonzo in “Fear and Loathing in Las Vegas,” Del Toro gained about 40 pounds and completely altered his speech. He so believably portrayed the maniacal Samoan attorney that it took the actor a while to get back to being offered “normal” roles.

Coolest Contribution: “Traffic,” 2000.

National Portrait Gallery, Eighth and F streets NW; Fri. through Sept. 7, free; 202-633-8300. (Gallery Place) 

Also on Express

Local chefs and bartenders are using cardamom in unexpected ways