There isn't a moment that better represents America's awkward relationship with football quite like Diana Ross spectacularly missing a penalty in the 1994 World Cup opening ceremony in Chicago. And the miss couldn't have come at a worse time.

The USA won the '94 World Cup bid largely to the disappointment and scepticism of the international football community. Prior to 1994, the US men's team had only qualified once since 1950: Italia '90, where they lost all three matches they competed in, scoring twice and conceding eight goals. America simply wasn't a football nation in the eyes of the football world – and, to be honest, our own.

Europe and South America's elite scoffed at the idea of a nation who would never appreciate the finer beauty of a 0-0 draw hosting the game's biggest tournament – an event we likely would not have qualified for if we hadn't done so automatically as hosts. Did the US simply flex its international-superpower status to win the bid? Almost certainly. Would American fans even bother showing up for a sport that didn't stop periodically for ads? Could the USA actually win a game this time?

With all these important questions looming in the background, the team resorted to a truly bizarre strategy. To manage the national squad they hired a certifiable football-madman in Bora Milutinovic, who preceded to select a squad of players who had played almost no professional football at club level. But that didn't matter to our boy Bora, because his plan was to hide them away in Southern California for an intense year-and-a-half training camp. So by the time the opening ceremony rolled through, the team had spent countless hours running on the beach, playing football tennis (exactly what it sounds like) against Bora and competing almost exclusively against other international teams. And with that, it was time for the rest of the world to take America seriously on the biggest sporting stage of all.

Enter: Diana Ross.

The opening ceremony was held at Chicago's Soldier Field, in front of a sold-out crowd of 67,000 people. Newly-elected President Bill Clinton gave a speech, Darryl Hall (of & Oates fame) sang, and Oprah emceed. Right at the beginning – just before a long, very-90s multinational procession of music and dance from participating countries – Ross appeared to represent America and one of its greatest exports: pop music. We should have known something would go wrong when Oprah (actually) fell off the stage right after introducing her.

Ross appropriately chose the 1980 hit "I'm Coming Out" to mark the debut of what would come to be known as the dawn of the new era of America's approach to the football.

As she took to the field, there was the usual fanfare: confetti, balloons, a football-shaped stage and a sea of dancers dressed in coordinated white costumes making way for Diana Ross as she raced the length of the field, uh, "singing". And then the moment came. It stared her down: a football and a goal. The fundamentals of the sport.

Ross lined up the penalty, took a stutter-step like the best pros do, approached, then back-pedalled for dramatic effect, and took another stutter-step, and then finally shanked the ball so far to the left of the goal it looked like a pass to the corner flag.

That miss alone was enough to live on in football folklore. But the cruel gods had one more treat. The goal itself was rigged to split apart when she scored – as if her shot, in its power and fury and accuracy, exploded it. But in preparations, the organiser never stopped to ask themselves: "What if she misses? What if she misses in front of the whole world? What if this international singer, singing in F Major and wearing heels, accidentally kicks the ball in a direction she did not intend to?"

When Diana missed, the goal – wonderfully, poetically – exploded in faux glory. "I want the world to know," she shouted, right after her tremendous whiff, as she jogged to the stage. The world already knew, really.

The metaphor was almost too palpable: America is good at many things. America is entertaining at so many things. America is bad at football. It must have been entertaining for the rest of the world to watch us pass out at our own house party. In one Chilean broadcast of the event, the commentator couldn't hold back his laughter. A live BBC radio announcer called the miss a "a dubious omen". Fusion also goofed on the singer's poor attempt.

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The supreme irony here, however, is that her gender and nationality would actually later come to represent the undisputed best in the world. The men, on the other hand…

In the end, the 1994 World Cup team and tournament exceeded expectations. The boys drew against Switzerland, defeated Colombia – which resulted in the murder of Andrés Escobar after he scored an own-goal (as if we needed a more stark contrast to how seriously other countries take soccer) – lost to Romania and achieved an impressively low-key 1-0 defeat to Brazil in the round of 16. Not to mention the fact that the average match attendance is still the highest among any World Cups.

Capitalising on this American "soccer-mania", the MLS was founded two years later. The '94 team solidified a kind of grit-and-grind counter-attacking style as our American identity, something that future teams would rely upon in place of overwhelming skill and talent. And the players and figureheads from that year would later come to run the game – then-burgeoning coach Bruce Arena led this year's failed team, and former player Earnie Stewart just filled the newly created role of US Soccer's general manager.