Willie Remember When: H&R Block Signed Nelson to do Super Bowl XXXVIII Tax Commercial

Some of you may very well remember Willie Nelson’s tax issues some time back. Thankfully, that’s not the case anymore, and not all he’s remembered for. But ironically, H&R Block found a way to bring light to their business and humor to Willie’s woes. The pair teamed up in 2004 to develop a commercial for Super Bowl XXXVIII (38) featuring Nelson with an “Advice Doll,” and the country-music-outlaw-turned-tax-specialist had another hit on his hands.

The tax preparation company (H&R Block) wanted to give Super Bowl viewers a gentle (more like hilarious) nudge that they needed to file at the very least, and otherwise, simply make good tax decisions. To do so, they incorporated Nelson’s wit with their prop “Willie Nelson Advice Doll,” pre-recorded with some humorous responses direct from Nelson himself.

Each person on the commercial obviously has a serious tax concern or question, beginning with, “Taxes are complicated! Is guessing a good idea?” Just pull the cord, and the doll cheerfully answers, “Willie would!” Other quirky responses the “Willie Nelson Advice Doll” gave were, “Correctomundo!”, and “I’m down with it,” proving that H&R Block found the Magic 8 Ball for tax questions, and it comes in a cute little Willie.