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Jomboy Media: A Breakdown

Jomboy Media

2023 Nominee ✨
  • Best Original Content or Series (Under 10 min)


Jimmy "Jomboy" O'Brien built a sports media empire off the strength, virality and lasting appeal of his "Breakdown" videos. These videos utilize Jimmy's unique approach to storytelling, combined with his original voice, insight and lip-reading commentary edited in an entertaining and informative style.

How does this represent “Excellence in Engagement”?

Since January 2021, each breakdown, on average, racks up more than 43.5K engagements across YouTube and social media.

Due to the high level of interest and engagement from audiences, we launched Jomboy Media Breakdown Shorts—a new YouTube channel that was created in the summer of 2022. This channel features short form highlights clipped from full breakdowns. In just a few short months, that channel has amassed 50K+ subscribers and more than 37 million views.



Jimmy "Jomboy" O'Brien's acclaimed "Breakdown" videos are popular and beloved because they are feats of storytelling. These are not merely highlight reels. O'Brien's talent is his ability to showcase magnificence in the seemingly mundane. He is able to take an ostensibly innocuous moment and stretch it out, demonstrating its depth and breadth, while highlighting the drama, humor, and absurdity of sports, popular culture, and beyond.

Breakdown videos began by focusing on baseball and have since spread into all parts of culture from basketball to cricket to ear-pulling contests, pickleball, lacrosse, Wheel of Fortune, and more.

Strategy & Execution

The strategy behind O'Brien's Breakdown videos is to follow the creator's passions. Though his videos often capture the zeitgeist, O'Brien only breaks down moments that he finds genuinely compelling.

That authentic interest is necessary due to the amount of sheer time and effort each video takes to produce. For each minute of Breakdown content, O'Brien spends at least one hour researching, analyzing, scripting, and producing it. That level of care shines through in the final product.

Breakdowns continue to resonate with people due to O'Brien's authentic curiosity and keen eye for detail. O'Brien will find a 20-second clip that no one else is talking about and elevate it into must-see viewing. He improbably turns ephemeral sports moments into evergreen content.


  • Jomboy Media


Jimmy O'Brien
Jomboy Media

Kyle Kondor
Head of Social
Jomboy Media

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