Chicago's Willy Wonka of Ice Cream

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As a child, Dana Cree refused to let her ice cream touch her cake. As an adult, she has no such qualms. One of the many flavors of prismatic ice cream bar produced by her Pretty Cool Ice Cream company features birthday cake-flavored ice cream inside a rainbow sprinkle shell. 

“We probably tasted 12 to 15 different cake flavorings, and it was probably the most disgusting tasting I’ve ever done, because those flavors really linger,” says Cree of finding the right flavor for the birthday cake ice cream. 

“Oftentimes when you go back and taste something you remember being so wonderful,” she says, “you find that it was actually pretty boring.” 

But Cree wants to harness that sugarcoated nostalgia while avoiding the disappointment, letting you keep your rose-colored glasses on when you eat one of her recreations of a classic flavor, like her upcoming state fair collection or a Dreamsicle. “It has to taste as good as you remember something,” she says. 

It was a homemade Dreamsicle that led Cree to focus Pretty Cool on ice cream on a stick rather than in a scoop – because it was better than what she remembered from childhood. She was doing an event for her cookbook Hello, My Name Is Ice Cream in St. Louis with a former colleague and had extra cream cheese ice cream base. Her friend suggested she put it in a machine his restaurant group owned that froze liquids into bars on a stick. They both loved the resulting treat, so she iterated, dipping her cream cheese pops into white chocolate flavored with orange and topping it with an explosion of sprinkles. 

“It was super nostalgic, but really modern and crazy delicious,” she recalls. “For two pastry chefs with 20 years [of experience] each to say, ‘I’ve never tasted anything quite like this,’ it’s something.”

She dreamed of ice cream on the drive back to Chicago from St. Louis, got to her apartment, and launched a Kickstarter to fundraise for her fledgling business. To describe herself, she wrote, “I’m Dana Cree, and I make…pretty cool ice cream.”

Ice Cream Is a Science (And an Art)

Before her brain froze onto ice cream, Cree made pretty cool pastries. She spent time at some of the most acclaimed restaurants in the world, from The Fat Duck in England to Noma in Denmark to Spago in Los Angeles and wd~50 in New York City. In Chicago, she worked at Alinea and found a berth with the One Off Hospitality group, receiving a local Jean Banchet Award and national James Beard nominations for her desserts at its Blackbird restaurant. Throughout this esteemed run, she started learning about the chemistry behind cooking, inspired by her “molecular gastronomy” chef colleagues who were making chocolate ganache retain a shape while being bent or creating fake lentils out of flavored solutions. 

An interest in food science became especially useful as she turned her attention to ice cream. 

“Ice cream is one of the most intricate foods we eat,” she says. “It is a liquid, a solid, and a gas at the same time. And getting those three states of matter to behave takes a lot of knowledge.” 

There’s a relatively narrow range of tweaks you can make in the ice cream process without messing it up and creating something that’s not recognizably ice cream. An inventive producer has to figure out how to manage ice, fat, sugar, protein, and air, getting them all to behave as a singular, scoopable substance that carries flavor and melts on the tongue, as Cree elucidates in Hello, My Name Is Ice Cream. Adding a new fat, like peanut butter, alters the texture. Changing the type of sugar affects how it freezes. Cream cheese has stabilizers that benefit an ice cream’s texture, while egg yolks incorporated into a base make it richer but also delay the release of flavor.

“It’s not like you use science to invent an ice cream, it’s that the science describes what’s already happening underneath the hood,” Cree says. “An understanding of it allows you to build your cuisine more creatively.” 

With help from colleagues, books, and an ice cream course at Penn State, she learned how to coax dairy, sugar, and flavorful ingredients into the ideal texture, selling pints of ice cream out of One Off’s butcher shop and compiling her knowledge in Hello, My Name Is Ice Cream in 2017.

And then she abandoned much of it. Because the ice cream for bars is “quiescently frozen” – that is, not churned – she had to develop new formulas when she launched Pretty Cool Ice Cream with Bang Bang Pie & Biscuits owner Michael Ciapciak in 2018. Her approach to toppings and add-ins had to change, as crunchy nuts or soft fruit sink to the bottom of a bar while it freezes vertically. And she had to start thinking like a chocolatier, since most of the bars are dipped in a cocoa butter-based shell.

But there is creativity to be found within constraints. “As soon as we tied our hands behind our back with this format, then the creativity really started to flow,” she says. 

Chocolate shells provide an extra layer of texture, flavor, and color; they allowed Cree to match the hue and sheen of a bar to that of several Porsches for a collaboration with the car company or to four train lines for one with the CTA. The shells can also hold or incorporate toppings, such as crushed-up pretzels and toffee to adorn coffee ice cream. (The pretzels, like everything at Pretty Cool, are gluten-free to adhere to Cree’s own dietary restrictions.) She’s added chicharrones from Carnitas Uruapan to the shell of a “Pigskin” bar for the Super Bowl and sprinkled crispy green beans and shallots on a cheddar-flavored shell for a Thanksgiving-themed green bean casserole bar. 

These flavors aren’t just novelties; each is meant to be enjoyed, not just tried out of morbid curiosity. “If it isn’t something good, we’re not going to put it on the menu just for kicks,” Cree says. 

Since bars aren’t churned, it’s easy to expand beyond dairy: Ice pops that foreground fruitiness, plant pops that are extra creamy. “It was very satisfying for me, in that I could include everybody,” says Cree. 

That accessibility was a major factor in her abandonment of high-end pastry for democratic ice cream. “The reason I left fine dining and wanted to do ice cream is because I was pouring my entire being into desserts that I can only share with people of certain means,” she says. “And I wanted to share what I did with everyone.”

Who doesn’t like ice cream?

Making 15,000 Bars a Week, (Mostly) By Hand

“Like most of you, my relationship with ice cream started so young, there isn’t a time I can remember without ice cream,” writes Cree in Hello, My Name Is Ice Cream. “When I was an adult and went to pastry school, and I learned how to make ice cream, it seemed nothing short of a magic trick.” 

Of course, there’s science and labor behind that magic trick. Summer is unsurprisingly peak season for Pretty Cool, which is currently producing around 15,000 bars a week at a new production facility. Previously, all the bars were made at Pretty Cool’s Logan Square storefront, where cookies for ice cream sandwiches are still baked. In the new facility, which isn’t open to customers, there’s plenty of room for increased numbers, allowing the brand to offer nationwide shipping as well as the possibility of another storefront and sales in large grocery stores in addition to the mom-and-pop ones it’s currently in. 

A surprising amount of the production process is done by hand. “If there is a machine that they can build that can do this, it’s probably a multi-million dollar custom line,” says Cree. 

There are at least six pieces of equipment involved in the production of a Pretty Cool Ice Cream bar. Take the s’mores bar, “probably the most complicated one we make,” says Cree. Marshmallows are toasted and then mixed into ice cream with hand blenders to give it a campfire essence. The marshmallow ice cream goes into metal molds, which are put in a subzero glycol bath that freezes them in about 10 minutes; the rapid freezing is essential for a smooth texture. Bars are then dipped in melted chocolate by hand, two at a time, and lightly swung to let excess drip off while the rest freezes on. Mini marshmallows and graham cracker crumbs are sprinkled over the top, again by hand, and the finished bar goes into a walk-in freezer. Finally, each individual bar is slipped into a package – yes, by hand – and sent down a small conveyor belt through a machine that seals it.     

The vibrant packaging is all designed by local artists, including Cree herself: The mango lassi, dark chocolate, and piña colada bars each feature her designs. “We’ve gotten to work with some really incredible people, and it adds this emotional layer to the ice cream that makes it feel like you’re unwrapping a beautiful present,” Cree says of the packaging. 

Collaboration is a hallmark of Pretty Cool, which has created more than 300 distinct flavors over its eight years. Some of the specialty grocery stores that sell Pretty Cool have signature flavors, like Agora Market’s Mediterranean-inspired bar or Piccadilly Market’s Banoffee pie. Thirty-five Chicago-area restaurants get tubs of ice cream or bars from Pretty Cool, with chefs like Thai Dang of HaiSous and Crying Tiger collaborating on flavors; his bar is inspired by Vietnamese coffee. There’s even an Eli’s Cheesecake bar.

“Dana is so creative that there are always more things to do,” says Pretty Cool’s pastry chef Aja London, who met Cree at One Off.   

Opening a company focused on ice cream bars, Cree says, “seemed like an uncharted creative path, in that the scoop shop had brought these elevated flavors, through Jeni’s” Splendid Ice Creams and other artisan brands. “But with the frozen novelty, it’s still relegated to the economy section of the grocery store and shapes like SpongeBob.”

Everyone wants to occasionally be a kid again, ecstatic at the sound of the ice cream cart bringing sticky SpongeBob pops to a park on a humid summer day. Pretty Cool Ice Cream helps fulfill that wish, bridging the gap between adult tastes and childhood memories while appeasing both. And that’s the beauty of ice cream, which harnesses scientific understanding for simple delight, drawing on deep-seated sentiment with an uncomplicated appeal.

As Cree puts it, “It’s really scientifically complex and very intellectually satisfying, but it’s also one of life’s simplest pleasures and emotionally connects so many people.”