"Ride him, cowboy!" is a classic phrase that harks back to the Wild West era of American history. It's typically used when someone is about to, or is in the process of, undertaking a challenging, or rough task, similar to a cowboy attempting to ride a wild horse or bull. The phrase is cheering encouragement, a hearty cheer rallying behind the "cowboy" to wing it and brave whatever wild ride lies ahead — be it an actual rodeo ride, or metaphorically speaking, any daunting task. High-action sports or trying moments in life can all be scenarios where this piece of old-time lingo might pop up. It's a wild way to say "Hang in there!”
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