Malone’s story—peppered with epithets and tales of ex-wives—gives a fascinating glimpse into American tattoo history. His connection with inking started when his sailor grandfather let him tag along to a shop while Gramps added to the anchors and ships that covered his arms. When Malone grew up, he became obsessed with photographing tattoos and started practicing his own work on “whoever would sit still.” Soon, he fell in with “big whips” like Ed Hardy and the late “Sailor Jerry” Collins, two pioneers who gave classic tattoos a shot in the arm by using better equipment and creating brilliant colors. When Collins died in ’73, Malone inherited his Honolulu tattoo parlor, changed the name to China Sea Tattoo Co., and tattooed “thousands of asses and just as many assholes” for nearly 20 years before closing up shop a few years ago.

Malone’s fabled past drew in Taylor Street’s owner Keith Underwood, who wanted to learn tattooing from a master. “I sought him out, started corresponding with him, buying machines and paintings from him,” Underwood says. “I’d send him my stuff, he’d say ‘I’m tired of all you young kids sending me this shit. It’s so bad you should just quit.’”

But Underwood didn’t. He packed up and went to work for Malone in ’99, honing his skills before opening Taylor Street last year, a place he describes as “a straight-up street shop where we tattoo panthers, roses, banners with sweetheart’s names.”

It’s the kind of shop where Malone felt like cooling his heels after years of runnin’ and gunnin’. “Keith and these other kids here, they’re genuine, no bullshit,” Malone coughs. “They can tattoo rings around me and do it in less time, but that’s just the way of things.”

Taylor Street Tattoo, 1150 W Taylor St, 312-455-8288, www.taylorstreettattoo.com.

Eastern elegance

If you’ve seen hot chicks walking around town with full-sleeve tattoos of brilliant saffron-red and cyan-blue Eastern deities, chances are you’ve already encountered the work of Kim Saigh. Her Wicker Park shop, Cherry Bomb Tattoo, is tucked away in the Flat Iron building with no flashing neon, buzzing tattoo guns or loud music discernible from the street. Saigh runs what’s just about the farthest thing from a “street shop,” catering instead to people looking for large-scale conceptual tattoos that take multiple visits to finish, work that Saigh calls “illustrative, narrative.”

Creating tattoos that leap off the skin to tell a story is a tactic she picked up working for famed tattoo artist Guy Aitchison. But Saigh is far from a copycat—she’s carved out a reputation for tackling fiercely detailed images like Hindu gods, lotus flowers, Japanese koi and spindly bonsai trees, and adding a soft, feminine flow to the work. Her designs crawl over the body, wrapping around arms, hips and shoulders. “Being a female tattoo artist has actually worked to my advantage, because some people really like having a woman do their work,” Saigh says. “I believe that women are more sensitive, so it must be a comfort thing, providing a nurturing atmosphere for people.”

That includes everyone from the aforementioned hot chicks to cops, lawyers, doctors, moms and even an elementary school principal who’s become a regular. “We’ve pretty much completely covered his torso with Hopi Native American designs,” she laughs. “We may not tell the kids’ parents, but we’ll probably still do more.”

Cherry Bomb Tattoo, 1579 N Milwaukee Ave, 773-645-1703, www.cherrybombtattoochicago.com.

Master of the macabre

It sounds like the setup for an after-school special: the loner kid sitting in the back of class, quietly drawing fire-breathing, plague-bringing creatures. Except on TV, the kid turns out to be a serial killer or ends up in rehab, and in our story, the kid becomes the hero—that is, to anyone who’s looking to get a dose of darkness permanently inked into their skin.

Our high-school doodler is Scott Fricke, who’s considered by many to be the local master of macabre: Demons, bats, blood, gore…if you can pull it from your worst nightmare, he can tattoo it. “My biggest influences, where a lot of this stuff comes from, I guess, were album covers, mainly heavy metal, and watching horror movies,” Fricke says. “That, plus I always was into art. My father and grandfather were both artists and I went to the School of the Art Institute…of course, just like in high school, I wasn’t really a great student. I was usually ditching class to go drink with the bums.”

After leaving the Art Institute, Fricke discovered H.R. Giger (who won an Oscar for his freaky-ass visual effects for the 1979 flick Alien) and began to develop his own bio-mechanic style of art. The 39-year-old artist has spent the last 14 years perfecting his signature style, which he now practices at Insight Studios, Chicago’s newest shop.

You can’t miss him—he’s the one turning a drawing of a demon biting the head off a baby into an art form.

Insight Studios, 1026 N Milwaukee Ave, 773-342-4444, www.insightstudiosonline.com.

The motley crew

In every arena, there’s a team that simply dominates. On the local tattoo scene, that team is Deluxe Tattoo. Owner Ben Wahh defines the shop’s philosophy: “Go beyond limitations, and work at ways of doing things that are unprecedented,” he says. And, most importantly: “Don’t even look at tattoo magazines or other people’s work.”

Wahh’s own work is a seamless marriage of tribal and biomechanical imagery that comes alive through trompe l’oeil, 3-D layering. But the humble Wahh is more likely to talk about his fellow artists than himself. “Tim Biedron is the busiest one here, with customers coming in from around the country,” Wahh says. “He uses muted colors and adds this dark quality to innocence, portraying tormented characters.”

As for the other artists at his shop, Wahh says Hannah Aitchison has overcome the stigma of being related to Guy Aitchison, an influential tattoo artist who left the local landscape a decade ago for the country, painting and penning tattoo books. “That’s a huge thing to deal with, being Guy’s sister, but she definitely has her own style, nailing portraits and really beautiful pin-up girls. Harlan Thompson is influenced by Japanese and American styles, but he doesn’t do it by the book, he creates a true hybrid of the two. Kevin Starai is an immaculate craftsman with a good understanding of color who does cartoon-y, goofy stuff that really reflects his personality. And Angel Silva’s main strengths are his black-and-grey work and his portraits.”

While all of the artists are in high demand (the wait for an appointment ranges from two to five months), Wahh is adamant about avoiding tat snobbery. “I don’t want someone to feel like they can’t walk in here and ask for a one-inch by one-inch piece of flash,” he says of the pre-made, non-customized designs that adorn the walls of most tattoo parlors. “We’ll put just as much into it and it’ll be the best one-inch by one-inch tattoo you can get.”

Deluxe Tattoo, 1459 W Irving Park Rd, 773-549-1594, www.deluxetattoo.com.

The sultan of script

When you go to what’s possibly the oldest tattoo shop in the city, you won’t hear a lot of high-minded notions about “artistic vision.” Instead, Chicago Tattoo—the Belmont Avenue shop that’s been serving up traditional tats since 1973—is typified by no-nonsense artists like Nick Colella. “I don’t fancy myself as anything but a regular tattooer; I don’t push what I think a tattoo should look like and I keep my opinions out of it,” Colella says. “I provide a service and I pride myself on giving clean, solid tattoos and giving people exactly what they want.”

What they want when they come to Colella is the traditional American style of tattooing often dubbed Sailor Jerry–style (women, nautical iconography, roses, daggers, etc.). As a young punk wasting days on Belmont, Colella would wander into Chicago Tattoo and study the black-and-grey lettering of artist Wayne Borucki, who convinced owner Dale Grande to give Colella a job when he turned 18. In the 13 years since, Colella has become known throughout the city for his lettering, having perfected everything from typewriter font to cursive script. It’s this last style that’s become his most requested when making the names of neighborhoods, cities and people indelible via ink. But it wasn’t always like this.

“In the early ’90s, believe it or not, the Tasmanian Devil was most popular; after that, it was barbed wire and tribal bands,” he laughs. “Now I get at least six requests a week for nautical stars, from people who don’t even know what they mean. At least with lettering there’s no confusion.”

Chicago Tattoo Co., 1017 W Belmont Ave, 773-528-6969, www.chicagotattoo.com.