Rippling’s First Super Bowl Ad Stars Tim Robinson as a Mastermind Foiled by Bad Software

Rippling is joining the big leagues of Super Bowl advertising with its first-ever Big Game spot, and it’s doing it with a perfectly on-brand mix of chaos and comedy. The HR and IT platform has tapped Tim Robinson—best known for “I Think You Should Leave”—to play a would-be criminal mastermind whose elaborate schemes keep getting derailed by one thing: terrible back-office software. In a Super Bowl filled with celebrity-driven super bowl commercials, this one stands out by turning everyday workplace frustration into the villain.

In the ad, Robinson’s character presides over a high-tech lair straight out of a spy movie, surrounded by henchmen and screens. But instead of being foiled by a caped hero, he’s undone by clunky systems that don’t talk to each other—broken payroll, scattered employee data, and IT chaos. The joke lands because it’s painfully familiar to anyone who’s wrestled with multiple HR tools at work. Rippling uses that frustration to position its all-in-one platform as the real secret weapon, promising to unify HR, IT, and finance so even an “evil genius” can’t mess it up.

This debut spot is a strategic move for Rippling, underscoring how high the stakes have become in the world of Super Bowl advertising. With 30-second placements now costing brands millions of dollars, the pressure is on to deliver memorable, high-impact creative that can break through the noise on game day and across social media. By pairing a distinctive comedic voice with a clear product message, Rippling is aiming for the kind of instant recognition that has defined some of the most unforgettable Super Bowl ads over the years.

For viewers who track every breakout moment from the Big Game, Rippling’s Tim Robinson spot will join a crowded field of tech, auto, and snack brands vying for attention. Whether it becomes a fan favorite or a cult hit, it’s another reminder that Super Bowl ads aren’t just about laughs—they’re a showcase for how brands translate complex products into simple, unforgettable stories. To see how this debut stacks up against other recent campaigns, check out more Super Bowl commercials from recent years.