As the month of June begins, the Windy City Gridiron staff is embarking on something we are calling the “30 Day Challenge” related to the Chicago Bears.
Each day of the month, there will be a new feature article published by one of our staff members on a unique topic. We’ll give our own answer to the question at hand, and then we’d like to hear from you all in the comments section.
For today, the topic is “Earliest Chicago Bears Memory.“
This one is easy for me. First, let me disclose my age. I’m 42
years old, I was just two years old when the Bears won Super Bowl XX. So, no, I have no memories of that game.
However, my earliest Bears memory is tied to the 1985 Bears.
Sometime around 1988, a new neighbor moved in next door to me. He was about my age (one year older), and he possessed something that would change my life: the Super Bowl Shuffle VHS. He also had a signed football by the 1986 Bears team (not as cool as ‘85, but close).
As a young, near elementary age kid, this Super Bowl Shuffle music video was one of the coolest things that I had ever seen. My friend and I would act out the video, over and over, while it played on the TV in his basement. He was always Walter Payton, and I would put on some sunglasses and portray Jim McMahon. It was a blast, and I doubt I’m the only one on staff that was doing this back in the 80s.
It should also be noted that, as most of our readers will know, the Bears were still a formidable team in the NFL at this point in time. In my young mind, I figured the Bears would be “shuffling” again pretty soon. And with this music video being one of my earliest exposures to NFL football, how could I not become a Bears fan?! That team was larger than life. That video tape was my gateway to fandom.
Needless to say, I’ve been waiting almost 40 years for the team to win another Super Bowl. Maybe 2026 will be the season. If you had told four year old me that I’d have to wait this long, I’d have never believed it. I might have still become a Bears fans, though. That music video was really cool.
As an aside, the earliest Bears game that I remember watching was the 1988 season’s NFC Championship game (played in January 1989) with the Bears being thoroughly dominated by the San Francisco 49ers, 28-3.
What’s your earliest Chicago Bears memory? Let us know in the comments!
