He’s been fired from an R. Kelly video, witnessed damage to one of the most iconic costumes in US brand history, and lost consciousness in a Thai operating room.
Greg Lilly lives an adventurous life, one shaped as much by his profession as by his down time.
Born and raised in Glenwood, Iowa, the 33-year-old freelance producer was “always interested in storytelling,” so it’s little surprise he ended up in an industry built upon it. Not only does he help others tell stories—whether by managing budgets, timelines, or creative talent—he also narrates his own via lived experiences, sometimes unintentionally.
Lilly began pursuing his career at the University of Northern Iowa in Cedar Falls, where he initially studied electronic media. After a professor told students that only about 6% of those majors went onto careers in that field, Lilly tagged on a business degree—a decision that’s served him well.
After graduating in 2012, Lilly headed to Chicago to intern at Ogilvy & Mather, an advertising, marketing, and public relations firm. “I was digitizing old tapes and was miserable,” he confessed of the steppingstone position.
The task-oriented job gave him entry into the field, and soon, he was doing freelance work for commercials and The Steve Harvey Show. Around that time, he found himself working on an R. Kelly music video.
“We had a celebrity dancer who was being paged to the set,” Lilly recounted with a chuckle. “I was standing right next to him and didn’t recognize him. He was very offended that I didn’t know who he was. They called me in and fired me.”
Lilly’s next stop was at the advertising agency McGarryBowen, also in Chicago, where he produced broadcasts, online content, test and radio spots, and edits for clients, one of whom was Kraft Foods, which owns the Hastings, Nebraska, brand Kool-Aid. For several years, Lilly was the unofficial guardian of the iconic Kool-Aid Man costume; a bulky, awkward fiberglass construction which embraced both the original costume and the updated fiberglass suit. He gamely gave himself the title “Kool-Aid Man costume creative consultant.”
Even after Lilly moved to Omaha in 2016 and went freelance with his own company, Greg Lilly LLC, he continued working with Kraft.
“I did all the live events for the Kool-Aid-Man,” he recounted. “Of course I tried it on; it smelled like the ’70s inside.”
In 2019, Lilly traveled to New York for a Kool-Aid Man skit on Saturday Night Live. Although he warned the stuntman to be careful with how he moved in the costume, he lost his balance and fell, cracking the iconic suit.
“I told him he needed to slide his feet,” Lilly explained, “but he lost his footing…”
Workplace anecdotes aside, Lilly has also experienced his fair share of global adventures from his home base in Omaha, and quickly became part of the cycling community. One year after moving to Omaha, he and five friends embarked on his first bike trip throughout the Iberian Peninsula. They began in Porto, Portugal, and biked to San Sebastián, Spain.
“We had forgotten how big mountains are,” Lilly conceded. “We did some ‘planes, trains, and automobiles’ and took transportation before getting on bikes again.”
About a year later, Lilly found himself in Thailand, where he and his partner, Sam, were in a motorcycle accident.
“I waited an hour for an ambulance, which was really more of a truck,” he recounted. “Sam used her legs to stabilize me during the drive, so I wouldn’t slide around.”
Once he arrived at the hospital, he was rushed to emergency surgery for a shattered collarbone.
“I drifted off to sleep staring at the different colored ceiling tiles wondering if they’d calculated my weight from pounds to kilos accurately for the anesthesia,” he said.
They did, and Lilly spent an additional month in Thailand recovering from his injury before returning stateside for corrective surgery.
His next overseas venture was tamer. In January 2020 he moved to Groningen, the Netherlands, with Sam, an outdoor recreation grant manager with the National Park Service. She studied public policy at a Dutch university for several months while Lilly made the most of the public transportation and bike trails.
“I loved the Netherlands. It was very refreshing,” he said. “I hung out, biked around, and talked with the locals.”
Unfortunately, the pandemic cut the couple’s time overseas short. They returned to Omaha, where he’s continued seeking adventure when and where possible. This past winter he spent “three weeks just not working” and 300 grueling miles (30 a day) cycling.
“There are two types of fun,” he offered. “Type one is obvious fun. Type two is fun—but hard.”
Friend Michael Hennings, an Omaha director, cinematographer, and filmmaker, accompanied Lilly.
“I like to call Greg ‘a fabulous blonde Viking,’” he joked. “I don’t want to say he’s a ‘leap-before-you-look kind of guy’ because in a subtle way, he’s calculated. He says ‘yes’ to life and just makes it look effortless. He’s inspirational to watch.”
For example, when the duo wound up in a small village where ATM cards weren’t accepted, Lilly found people willing to accept a Venmo payment in exchange for cash. Of course, they ended up enjoying a meal together later for dinner.
“When you’re a producer, 90% of what happens is planned,” Hennings noted. “10% is where the magic happens. Greg is observable magic.”
What’s next on Lilly’s list? Possibly a cycling trip to Lake Michigan or one to Colombia, depending on the country’s political state.
“It’s a big world,” Lilly said. “I’ve always been into stories—hearing other people’s and making my own.”
This article originally appeared in the May 2023 issue of Omaha Magazine. To receive the magazine, click here to subscribe.
