Elvis Costello likes vanilla ice cream bars dipped in dark chocolate with almonds. Ben Gibbard of Death Cab for Cutie has a taste for Bomb Pops. Kanye West, Sufjan Stevens, the Arcade Fire, and the Dears all favor Julie’s Organic ice cream. And Matt Allen has served them all.

Over the last three years, Allen has trekked more than 35,000 miles in a 1969 Chevy Step Van to hand out free ice cream at the country’s largest music festivals. He estimates that he’s given away nearly 100,000 frozen treats to date. It’s not enough for people to think of him as an ice cream man; Allen wants everyone to know him as the ice cream man.

“The term has over 50 years of goodwill attached to it, yet there’s no face, no image, no brand, no company, no logo. There’s nothing,” he says. “My idea was that I could make myself the Ice Cream Man so that when people think of ice cream, they’ll think of me.”

Last summer Allen hit three of Chicago’s biggest outdoor festivals: Pitchfork, Intonation, and Lollapalooza, where he got a plug from Jack White in front of 40,000 people during the Raconteurs’ set. This weekend he’s returning to Pitchfork, where he’ll be dishing out sweets all three days.

Allen, who won’t reveal his age, grew up in Long Beach, California, and attended Fort Lewis College in Durango, Colorado, where he studied accounting and finance. It was there, during his last summer break, that he launched his first ice cream operation: a three-wheel bike, a cooler, and a boom box. An avid adventurer who’d once spent a month traveling cross-country to ride roller coasters–100 in all–Allen graduated in 1998 and spent the next several years on the road. He hiked the Appalachian Trail from Georgia to Maine and the Pacific Crest Trail from Mexico to Canada. In 2001 he biked to Maine from his home in Long Beach to raise money for cancer research. On every trip he hit every chocolate and candy factory he could find.

“People grow up and think they have to give up the things that made them happy when they were younger,” Allen says. “That makes absolutely no sense to me.”

In 2002 Allen took a job at a chocolate factory in Ashland, Oregon. He says Willy Wonka has always been an influence, and working at the factory was the fulfillment of a lifelong dream. But he left six months later when a new general manager was brought in, then spent the next few months in Austin, where he helped reopen the infamous dive bar and music venue Hole in the Wall.

Less than a year later, after returning from a backpacking trip to Hawaii, Allen heard from a man in Ashland who was looking for someone to take over the ice cream route he’d worked for nearly 20 years. Allen made his way back to Oregon, bought an ice cream truck for $1,200, christened it Bessie, and took over the route under the name Ice Cream Man. He struggled to turn a profit, and at the end of his first full season he decided to throw an ice cream social at a city park, giving away the rest of his inventory. “There was a line the length of a football field, all ages, waiting for free ice cream, and everyone was just so happy,” he says. The event was an epiphany. “If I’m not going to make any money selling ice cream,” Allen says he realized, “why not find a way to give it away?”

He stumbled on the solution while working as a vendor at the 2004 All Tomorrow’s Parties festival in Long Beach. “I drove back home the second I heard the Flaming Lips and Lou Reed were going to be there,” he says. “I just had to be a part of it.” That was the last time Allen charged a customer for ice cream. “That night I realized the connection between the audience at music festivals and the companies trying to reach that demographic,” he says. “All I want is to do is give away free ice cream; it’s that simple. This seemed like the most logical way to do it.”

Allen started seeking sponsorships on a project-by-project basis to cover his costs at regional events like Coachella and ArthurFest, offering Bessie as a mobile billboard. He launched a Web site, icecreamman.com, where he and a crew of volunteers would post reviews and photos of shows Allen had worked. Sponsors started signing on. Today Ice Cream Man has steady relationships with Levi’s and Guitar Center, online services like GameFly and Rhapsody, and ice cream brands like Julie’s Organic and Mochi. Toyota gave him a Yaris hatchback tricked out as a “Bessita” and Warner Brothers recently used him to promote the new White Stripes album, Icky Thump. The record blared from Bessie’s speakers while Allen handed out desserts in boxes custom designed by Rob Jones, a graphic artist who’s worked with the White Stripes for years.

Allen says he’s never wanted more than to break even, but even that’s no picnic. “These sponsorships barely cover my costs, and it’s for a very short period of time. I’m living in my mom’s house right now. I sold my 1969 Chrysler Newport. I’ve sold nearly everything I’ve owned.” During the winter he supplements his income with odd jobs in Long Beach, like putting up and taking down Christmas lights.

It doesn’t help that Bessie isn’t the most reliable ride. In the last year and a half Allen has had to replace the ignition, carburetor, engine, and radiator, not to mention brakes and tires. There’s no air conditioning or cruise control, and most nights Allen sleeps on top of the freezers on an inflatable mattress. “You find ways to make it happen,” he shrugs. “You sleep on the side of the road, sleep at Wal-Mart, sleep at rest stops, get kicked out of parking lots at 3 AM ’cause you’re not supposed to be there. It’s life.”

Bessie’s odometer broke years ago, but Allen guesses he’s logged more than 5,000 miles this summer alone. He’s already driven from the Virgin Festival in Vancouver (his first Canadian venture) to Bonnaroo in Manchester, Tennessee, with pit stops at the Sasquatch Music Festival in George, Washington, and Wakarusa in Lawrence, Kansas. From Pitchfork he’ll head to the 10,000 Lakes Festival in Minnesota, make a return trip here for Lollapalooza in August, then maybe head overseas for Big Day Out in Australia or the Iceland Airwaves Festival, if he can line up enough sponsors.

Allen plans to try three more summers on the road before moving on to something entirely new. “This has always been about something bigger than giving away free ice cream,” he says. “The purpose is to show people that nontraditional business ideas can succeed. There are ways to do it. You can achieve your dreams. You can love your job.”

Art accompanying story in printed newspaper (not available in this archive): Matt Allen photo by Matthias Ingimarsson.