F. Scott Fitzgerald’s The Great Gatsby is a staple of high school English classes and “best books” lists, from 20th Century books to American novels to the greatest novels ever written. Therefore although some Gatsby fans have merely ogled Leonardo DiCaprio or Robert Redford in the titular role (in one of the unspectacular film adaptations of a hard-to-adapt novel) most of us have actually read the book. To us, it may feel like Tom and Daisy Fay Buchanan, Nick Carraway and Jay Gatsby have always been around. But did you know Gatsby languished in obscurity for years? The American classic, which celebrates 90 years of publication today, has a backstory as convoluted and fascinating as the enigmatic, self-made Gastby’s himself.

To celebrate Fitzgerald’s critique of, and ode to, jazz age capitalistic excess, here are five interesting angles on the novel and its history for your consideration.

1. An original proposed title for the novel was the biggest clunker ever: Trimalchio in West Egg. Another was Under the Red White and Blue. Hard to imagine Jay-Z scoring a soundtrack to a movie with one of those titles, isn’t it?

2. World War II helped bring Gatsby back, after Fitzgerald died thinking it was a failure, even being unable to find it in bookstores. The Council on Books in Wartime program that printed American Service Editions of novels for World War II was pivotal in cementing Gatsby’s reputation as a classic:

Gatsby entered the war effort after Germany and Japan surrendered, but the timing was fortuitous: While waiting to go home, troops were more bored than ever. (Two years after the war ended, there were still 1.5 million people stationed overseas.) With that kind of audience,Gatsby reached readers beyond Fitzgerald’s dreams. In fact, because soldiers passed the books around, each ASE copy was read about seven times. More than one million soldiers read Fitzgerald’s Great American Novel…. For Fitzgerald, it was a great reawakening. The author’s death in 1940 had rejuvenated academic interest in his work, and many of his literary friends were already trying to revive his name. But the military program sparked interest among a wider, more general readership. By 1961, The Great Gatsby was being printed expressly for high school classrooms. Today, nearly half a million copies sell each year.

3. Why was Gatsby out of vogue to begin with? Because it was a huge flop, and many critics mauled it when it first appeared. Not only did the book fail to print the copies Fitzgerald expected, but it took a general critical drubbing.

The New York Evening World called the book “a valiant effort to be ironical,” but “his style is painfully forced.” The daytime version of the paper ran a headline that called Gatsby “a dud.” Isabel Paterson wrote, “What has never been alive cannot very well go on living; so this is a book for the season only.” In the Chicago Tribune, H.L. Mencken pronounced it “no more than a glorified anecdote, and not too probable at that…. Certainly not to be put on the same shelf with, say, This Side of Paradise.”

Nowadays, when you read Gatsby side by side with This Side of Paradise, it’s easy to see the latter as an obvious “first novel” and the former as a more mature, complex culmination of a writer’s thoughts and talents. But Gatsby still remains a subtle book despite the excesses it contains, which readers of the time clearly missed.

4. In fact, some of the novel’s sharper criticisms of its depicted milieu are commonly misunderstood even today. As Zach Seward wrote in a memorable piece right before the DiCaprio vehicle arrived in theaters:

So many people seem enchanted enough by the decadence described in Fitzgerald’s book to ignore its fairly obvious message of condemnation. Gatsby parties can be found all over town. They are staples of spring on many Ivy League campuses and a frequent theme of galas in Manhattan… It’s like throwing a Lolita-themed children’s birthday party.

Whenever someone throws a Gatsby party, I get the urge to yell, “he was shot to death alone in a pool, you idiots!”

That having been said, perhaps some of the common misreading is due to the fact that Fitzgerald, like his contemporary Edith Wharton and other sharp social critics, was known to have had something of a love-hate relationship with the ultra-rich. Although the book ultimately shows the hollowness of their lifestyles, so does it detail the seductiveness of the blithe existence of “careless people” like Tom and Daisy Buchanan. Like Jane Austen, like Robert Frost and many other easily accessible writers, one has to dig beneath the surface to find the darker message.

In his piece, Seward also casts a dubious eye on the contemporary high school teachers who use the “green light” that Gatsby gazed at to teach students to “strive.” Today the light is often spun into something noble, waiting to be seized by those who persist and imagine, rather than what Carraway and Fitzerald see it symbolizing: a false hope, always receding, embodying what Seward calls the “novel’s jaundiced view of the American dream.”

5. Fitzgerald loved, then hated, the iconic “eyes” cover design for the novel, and may have even rewritten part of the book in response to an initial look at the cover art by Francis Cugat.

In a letter to editor Max Perkins, Fitzgerald, whose manuscript was late, requested that the art be held for him. “For Christ’s sake don’t give anyone that jacket you’re saving for me,” Fitzgerald wrote, “I’ve written it into the book.” It’s not clear exactly what Fitzgerald meant by this, but it is generally believed that that Cugat’s haunting image was realized in the form of the recurring billboard for oculist Dr. T.J. Eckleburg…

It’s unclear which iteration of the cover design influenced which part of the book, but they were more symbiotic than we realize, and both grew into icons over time.

The irony of imagining “Scotty” searching in vain for his book in stores’ shelves mere decades before it was thrust into the hands of millions of soldiers and then schoolchildren is nearly too painful to bear. Of course, agonizing missed moments are the subject matter make Gatsby the masterpiece it is.