Remember when kids weren't just walking through stores—they were gliding? Heelys burst onto the scene in 2000, the brainchild of Roger Adams, who reportedly came up with the idea while pushing his son in a stroller. He watched skateboarders and rollerbladers and thought: what if shoes could do that? His answer was embedding a wheel in the heel, creating footwear that could instantly switch between walking and rolling with a simple shift of weight.

The timing was perfect. Heelys hit peak popularity in the mid-2000s, becoming the must-have item that drove parents crazy and store managers to distraction. At their height, the company was selling millions of pairs annually and even went public in 2006. But here's the wild part: they became so popular that they also became banned. Malls, schools, and airports started posting "No Heelys" signs faster than kids could roll through them. The liability concerns were real—emergency rooms reported thousands of injuries, mostly broken wrists from spectacular wipeouts.

Despite the controversy (or maybe because of it), Heelys became a cultural phenomenon. They were featured in movies, worn by celebrities' kids, and sparked endless debates about whether they counted as shoes or vehicles. The company struggled after the initial craze died down, filing for bankruptcy in 2009, but Heelys never truly disappeared. They're still sold today, quietly maintaining a cult following among nostalgic millennials and adventurous Gen Z kids who've discovered the joy of heel-rolling through life.