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Remember When Willie Nelson Starred in a Super Bowl Commercial?

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He’s one of the most legendary artists in country music history, but Willie Nelson still doesn’t take himself too seriously.

In the 1990s, 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 a Willie Nelson 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.

Fortunately for Nelson, friends and supporters of his showed up when the IRS auctioned off his possessions, buying much of his property and giving it back to him. He ultimately settled his debt for right around $9 million, releasing an album titled The IRS Tapes: Who’ll Buy My Memories? to help raise the cash he needed.

NEXT: Remember When Tim McGraw Had Long Hair?

Willie Nelson and More Country Stars Who’ve Suffered Tragedy

Do You Know Everything About Willie Nelson?

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