Income Tax Show

Two IRS agents visit Jack. They can't understand how he could have earned 375,000 dollars, and spent only 19 dollars on entertainment. Since one declared item was 3.90 (three dollars and ninety cents) to take Mr. and Mrs. Jimmy Stewart to dinner, they next visit the Stewarts. The Stewarts reveal that on the occasion in question, Jack saw them at their favorite restaurant, made them sit at his table with his waitress/girlfriend, told them he would pay, and then at the end generously let the Stewarts pay the whole bill so they could have the tax deduction. The 3.90 was for cleaning his suit after Gloria Stewart dumped the salad on his head.

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S15E05 - Jack Makes a Comedy Record