Remember “the mixtape era?” No, not that awkward period when you sent cassettes of angsty love songs to unsuspecting high school crushes. I’m talking about that magical moment in the mid to late 2000s when rap music underwent radical innovations in the way it was made, distributed, and discovered. Ditto for album cover designs, which are as loud and confrontational as possible—but with good reason. Like the music, they satisfy the imperative to stand out and draw people in by any means necessary. Rules be damned.

Unlicensed images, logos, outlandish violence, and all manner of criminality are fair game, as long as the design makes an immediate impact and excites a listener to give it a try. Cover art was critical in order for a mixtape to stand out from the pack, and the high demand for graphic design spawned a cottage industry of virtuoso Photoshop wizards. But unless you were an avid collector during this era, the real design gems will remain hidden. Fortunately there’s Damn Son Where Did You Find This?, which documents some of the best cover art of the period and pays homage to the artists behind this dense, surrealist genre of chaotic maximalism; and the previously sold-out book is (finally) available again.

In this post-Napster, pre-Spotify moment in music history, mixtapes allowed artists to self-release music directly to fans (primarily for free online) and bypass an industry of publishers, labels, and distributors that would often compromise their artistic freedom—or prevent them from being heard altogether. The production value was scrappy, but effective. Rapping over unlicensed music, “borrowing” vocals from other artists, and all manner of other copyright violations were hallmarks of the genre. The vacuum of legal regulation and absence of record label intermediaries allowed for artists to create music by a doctrine of total creative openness. This spurred a vanguard of artists who would drive mainstream rap for the next decade. Lil Wayne, Rick Ross, Dipset, Gucci Mane, and many others built early fan bases by exploiting the mixtape market, bypassing a risk-averse music industry that was often unwilling to take a chance on them.

As a fan of this era of rap music (I’ve even lectured on the topic at Kalamazoo College), I have to confess that much of the cover art for these mixtapes blurs together in my mind as a psychedelic tableau of movie posters, Scarface references, mountains of cocaine, purple (the color), lens flares, and exhibitionistic doggystyle fucking.

On their own, the covers are difficult to decipher, and on the whole the genre is completely overwhelming. But Damn Son guides the reader through by letting the designers put it the work their own words. “You can look at this art 100 times and find something new every time,” says Michael Thorsby, who designed and co-authored the book with Tobias Hansson. “There is logic in this art that seems so illogical, so we felt it was important to tell the story of the covers in the words of the people that made them.”

For the designers, the unbridled creative nature of mixtape art is liberating, but like any art form, there are always constraints. For mixtape design, it’s time. With no legal or contractual barriers, rappers release mixtapes as quickly as they can make them. In order to keep up with demand, the designers in Damn Son produce covers at an astonishing pace. KidEight, who has designed work for Rick Ross, OJ Da Juiceman, and multiple covers in the Tapemasters & DJ Envy “Purple Codeine” series, says, “In the last 30 days, I have probably done 70 [covers], but I’ve done 18 in two days a couple of times.”

The time limitations force designers to develop shortcuts (not unlike those used in more formal design industries); toolkitting, a shortlist of go-to Photoshop filters, and elaborate image banks are just some of the means by which mixtape designers can produce at such volume and not sacrifice quality. According to Thorsby:

“The craft is absolutely incredible. One of the designers sent me a PSD, by mistake I assume, and the file structure was out of this world. It was like some kind of alien signal reaching the earth.”

The designers in Damn Son also impose their own creative constraints, which lead to some key of the aesthetic differences. For example, Tansta applies an element of reality to his work. In a style of visual art characterized by extreme, often comically cartoonish imagery, he stands out by holding his art to a modicum of plausibility.

“Pounds of drugs laying on the floor or money laying on the concrete, where does that happen? What the fuck! This is stupid. It doesn’t make sense. Who would do this? Who would leave thousands of dollars on the street in the hood?”

Can’t argue there.

Client requests can also push an artist’s moral limits, forcing them to grapple with their own values to reconcile what they are and are not willing to depict on their covers. Miami Kaos describes balancing his Christian faith with the occasionally violent concepts his clients’ request: “I designed a cover… on the theme of New York vs. The South. I had Jay-Z picking up Lil Wayne by his throat and Jay is simply shooting Wayne. People knowing me who saw it were like ‘Don’t show this to anybody’… So I buried that work.”

Other designers relish the opportunity to push these boundaries. KidEight, who’s cover for Rick Ross’ Fuck the Rap Game, features 50 Cent’s decapitated head and Young Jeezy’s dead body hanging from a meat hook, says, “I have no morals. Obviously there are subjects that I wouldn’t do… I always enjoy a cover where you can push boundaries… I think it’s pretty hard to shock people, in general, nowadays.”

Current events feature heavily across all of the portfolios in Damn Son, often as a technique to signal the “freshness” of a mixtape. Pegging cover designs to the news of the day is a quick shortcut to communicate that a release is new, and like many trends in mixtape design world, these themes are rapidly adopted and spread across the industry. “The week after Hurricane Katrina there were mixtapes with hurricane Katrina covers. And you knew that for the next few weeks there would be more because that’s how you knew it was fresh,” says Thornsby.

It’s easy to see why novel ideas quickly become tropes for these artists. When designers are producing at this volume, often with very little creative input (“make it hood” is a common brief), it’s wise to use shortcuts and an array of gestures and scenarios that have proven to work.

For example, throughout the book there are dozens of slight variations on a similar scene: the rapper is being pursued by police, standing behind an enormous pile of cocaine and/or money, while counting more money, and somewhere in the foreground, there is a butt. Does it stand out? Yes. Is it “hood?” Almost certainly. Did it take more than 90 minutes to create? Not likely, and that’s a good thing in a functional, high-volume school of graphic design where speed is a component of quality.

And this is Damn Son’s greatest achievement as a tribute: it reveals the idiosyncratic systems and standards of mixtape cover design, and shows how the cover art is not only vivid and fantastic, but also thoughtful, deliberate, and utilitarian.

The book arrives at an appropriate inflection point in the music industry. With the rise of Spotify and other music streaming services, people are discovering new music through highly sophisticated recommendation algorithms. This changes the role of cover art from that of an advertisement for the music, to more of an aesthetic companion. And both the music and the visual art have to be free of copyright and trademark infringement in order to be hosted on these services in the first place. As a result, the market for renegade mixtape art is drying up. So Damn Son Where Did You Find This serves as a timely reflection on a moment when a lack of regulation, a music industry in flux, and a few Photoshop hustlers in an unheralded corner of the design world collided to make some serious noise.

Damn Son Where Did You Find This? is now available in the U.S. from Walther König.