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Remember When Willie Nelson Starred in a Super Bowl Commercial?

Willie Nelson
Rick Diamond, Getty Images

In the early ’90s, Willie Nelson learned he owed the IRS millions of dollars because his accountants hadn’t been paying his taxes for years. The amount was lowered to $16 million, but the singer still had to sell anything that he could to pay off the massive debt. During Super Bowl XXXVIII, almost 15 years after Nelson had his issues with the IRS, America clearly hadn’t forgotten. This spot for H&R Block was amongst the funniest of the year. “Taxes are complicated. Is guessing a good idea?” a frustrated do-it-yourselfer asks the Willie doll. “Willie would,” the doll answers. Nelson has never shied away from poking fun at his legal issues, and he alone makes this commercial so much fun and effective. Look for a cameo from (then) Yankees coach Don Zimmer at the very end.

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Watch Willie Nelson’s H&R Block Super Bowl Commercial

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