Willie Nelson in H&R Block’s 2003 Superbowl XXXVII commercial

by: Aviva Okeson-Haberman

In this commercial, which ran during Super Bowl XXXVII, the Kansas City-based tax preparation giant spoofed the country music star Willie Nelson’s well-documented troubles with the IRS. 

In the spot, Nelson is promised “huge money” if he stars in an ad for a fictional shaving company. “It’s not about the money,” Nelson’s agent responds. “This is Willie Nelson.” After finding out that he owes the IRS $30 million, Nelson quickly agrees to the ad. 

Nelson got in real-world trouble with the IRS over millions of dollars in delinquent taxes in the 1990s. He released an album called, “Who’ll Buy My Memories? (The I.R.S. Tapes)” to help pay off some of the debt. 

In 2004, H&R Block again featured an ad with Nelson that poked fun at the singer’s tax troubles. This time with a Willie Nelson advice doll that gave out bad tax advice. 

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