Editors Note: Reel Chicago’s The Reel Black List isn’t just about February—it’s about honoring the Black creatives, leaders, and visionaries who shape Chicago’s film, TV, advertising, music, and media industries year-round. At a time when DEI initiatives face increasing challenges, it’s more important than ever to acknowledge and amplify the voices making an impact. For the next 29 days, we’ll celebrate the incredible contributions of Black professionals across the city. But let’s be clear—Black excellence isn’t just a moment. It’s a movement. It’s 365. Today, meet award-winning chief creative officer, Robert Clifton, Jr.
Robert Clifton Jr. is best known for creating the character Wario for Nintendo and leading the team that created the Scissorhands Super Bowl commercial for Cadillac. Currently, Robert is the Chief Creative Officer of Contender, a Chicago-based ad agency he co-founded with Kristian May.
What’s your Origin Story?
I’ve been blessed with an overactive imagination so I spent my early childhood years drawing, which then led to my art being on display in the mall. In my formative years, my overactive imagination came in handy as I excelled at playing the dozens. My creativity would later spill over into moves on the football field and the basketball court. So it felt natural that I would pursue a career in advertising.
So after studying marketing at Hampton University and advertising at Norfolk State University, I attended the prestigious Portfolio Center, which led to my first job as an associate copywriter at Leo Burnett, and a career, bouncing back and forth between General Market agencies and Multicultural agencies, until I co-founded Contender, which we like to call a challenger agency.
What did you want to be as a kid?
When I was a kid, I thought about what I might do for a living, but my real focus was on what I would drive. So while I wasn’t sure about whether I would be a writer, a painter, a pro football player, an architect, a lawyer, or even a comedian,
I knew I wanted to be rich enough to drive a Ferrari. It has been the one consistent goal in my life since I was 7 years old.
How did you choose your career path?
I was watching the Super Bowl and found myself mesmerized by an ad that asked the question–If you were a car, what car would you be? In my head, I replied, I would be a Ferrari. The commercial proceeded to show a driver’s POV of a car accelerating around curves, until the end where it’s revealed that the car you’ve been experiencing, is a Porsche. I said to myself I can come up with ideas like that. I’m going to do TV commercials. From there I locked in.
What’s your creative process like?
Chaotic and unsettling, but worth all the stress, when you arrive at my favorite part of the business, that eureka moment, when somebody says, that’s it!!!
Who inspires you?
I’m inspired by characters from movies. Underdogs like Wendell Scott from Greased Lightning, Luke Skywalker, Rudy and Willow, whose story arcs drive me to stay the course in pursuit of the impossible.
The most unconventional risk you’ve taken in your career?
Leaving the big production budgets of the general market side of the business at the height of my career to go play at a Multicultural agency. Was one of the best moves I made as it taught me how to be scrappy with smaller budgets and how to reach the customers driving culture–as well as purchase decisions.
When faced with setbacks, what keeps you going?
The belief that every setback is a set up for a comeback.
Your favorite Chicago Dive.
It’s far from a dive, but Virtue in Hyde Park is a place I love to post up for amazing food and drink, and an interesting crowd to boot.
List in order of love: Bears, Blackhawks, Bulls, Cubs, White Sox.
White Sox, Bulls, Bears, Cubs, Blackhawks.
What’s on tap for 2025?
More disruptive forms of storytelling like the 4-minute animated short “The League of Black & Unlimited Dads” as we build and grow Contender into one of the world’s most preeminent ad agencies.
Linus has his blanket for comfort, you have…
At Contender we have a team of outliers challenging me with disruptive ideas for new approaches, innovative tools and techniques, and disruptive models each and every day, so that I don’t get comfortable.
Some of Robert’s work:
To see others on The Reel Black List, click here.
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