The adulatory use of the word “cool” is often credited to Lester Young, the tenor sax man, but the provenance is somewhat murky. Less uncertain, however, is that the term, no matter its definition, is a description many seek: from celebrities posturing on screen and in print to the rest of us strategically oversharing everything from our musical tastes to the contents of our breakfast via Facebook and various other social media platforms that end with the letter “r.” The quest for cool is an ongoing and noxious obsession.

So you can’t really blame the National Portrait Gallery for its latest exhibit. On the second floor of Washington’s Old Patent Office Building, the word “cool,” brought to life by blue neon, beckons visitors to this glittering pictorial gathering of America’s 100 greatest antiheroes.

You might ask: What, exactly, constitutes coolness, and how does one quantify it? Is it not an entirely relative and personal matter? After all, even the oft-maligned melon-smasher Gallagher has a devoted following. Enter Joel Dinerstein and Frank H. Goodyear III, the show’s curators, who have embraced the difficult task of figuring out just who are the coolest 100 Americans of all time. To accomplish this, they asked that candidates possess an original artistic vision, be instantly recognized by the masses, leave behind a “recognized cultural legacy,” and flash the proper amount of rebellion. Add these up and, as we will see, only entertainers are capable of high-level coolness: Jonas Salk, for example, and Chuck Yeager are not cool. In any case, one gets the drift that the rebellion quotient was paramount in the selection process. “This is a nation born in revolution, a country [that has] always valued rebellion,” Dinerstein explained to the Washington Post earlier this year.

From George Washington to Susan Sarandon, we’re a nation of rebels.

Accordingly, a visit to “American Cool” can charitably be described as akin to a stroll through a three-dimensional copy of Rolling Stone, complete with echoes of that magazine’s politics. Here’s Johnny Cash, the Zeus of country music, a man who knew of “the rocky quest for redemption as walked by the fallen and disenfranchised,” posing pensively in front of Folsom Prison. And there’s Willie Nelson, that “tireless advocate for marijuana legalization.” (No mention of the Taco Bell commercials the pair cut back in the 1990s.)

Bruce Springsteen, the blue-collar bard who “considers his art a job of social leadership,” isn’t far away, looking typically earnest. A portrait of Jon Stewart, known for his “even-handed interviewing style,” is down the hall, looking typically smug. The rocker and the satirist also share the invaluable ability to transform from social commentator to entertainer when effectively challenged on their opinions.

Elsewhere we find the usual timeless icons (Brando, Bogart, Dean) and the expected lineup of acclaimed boozers (Burroughs, Thompson, Pollock), a millionaire hip-hop mogul (Jay-Z, “the synthesis of American culture’s love of outlaws who live in opposition to cultural approval”), a pop diva (Madonna, “an early activist for gay rights”), lots of other New Yorkers (Lou Reed, Patti Smith, Debbie Harry, David Byrne), and at least one Communist (Angela Davis, whose “afro is an example of cultural politics through style”).

The inane labels underscore this exhibit’s most significant flaw: Whatever you think of the subjects, it’s undeniable that many of the photographs are striking; but the visitor learns almost nothing about the portraits themselves or the artists who created them. Instead, we are treated to the idols’ cool narratives, which alternate between prosaic, as we have seen, and ridiculous (Missy Elliott: “In her phantasmagoric videos, Elliott dances coolly in space in colorful jumpsuits”) and panting (Chrissie Hynde: “In leather jacket or muscle shirt, holding her Fender Telecaster lightly, Hynde sings out from under dark bangs and darker eye makeup”).

Sure, this may captivate some, but short of investing in the catalogue ($49.95), visitors are on their own when it comes to ferreting out the facts behind the portraits. And given that this is the National Portrait Gallery, that is unfortunate.

For example, it would be nice to know more about Thomas Hoepker’s photograph of Muhammad Ali, in which he is raising his fist to the lens while sitting on a bridge with the Chicago skyline in the distance. The same goes for a charmingly casual photo of Jimi Hendrix snapped by Linda McCartney. And William Claxton’s photo of Steve McQueen driving (no doubt speeding) in his Jaguar XKSS. There is also a famous image from Elvis Presley’s triumphant return to Tupelo at the Mississippi-Alabama State Fair and Dairy Show in 1956.

Visitors won’t likely see or discover the context. Instead, we get didactics that read like fan club letters. In the case of the King, we get quotes from fellow cool guy Bob Dylan and from John Lennon (who would have made the list if he had lived long enough to become a U.S. citizen) vouching for Presley’s coolness, lest anyone question it. But the exhibit—categorized by eras, and dipping back into the 19th century—is strongest when exploring the early 20th century, or “The Roots of Cool.” The less affected subjects here, such as Duke Paoa Kahanamoku, the Hawaii renaissance man who helped popularize surfing, are less familiar and may even encourage visitors to do some research of their own.

This is a vivid lineup of acclaimed and interesting artists, writers, and other entertainers. But the entire premise of “American Cool,” like a fair number of the men and women represented here, is arch and preening. It also makes one question the value of cool. As used here, it too often describes aloof, indulgent, tragic characters whose rebellious gestures seem slightly choreographed. John Wayne, who made it into the exhibit despite his conservative politics, describes his “rebellion against the monotony of life”—although the quote, not given in full, was actually a swipe at Students for a Democratic Society. “American Cool” gives one the faint urge to rebel against the monotony of our obsession with coolness and our glorification of celebrities and their culturally sanctioned “rebellion.”

Ryan Cole is a writer in Indianapolis.

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