10. A ‘Playmate’ Party The tax returns
How he pulled this one still amazes me. The owner of a nightclub promotions firm concluded that a regular party just wasn’t cutting it for his clients. So, he brought in a bunch of scantily clad “bunnies” as decoration. The tax courts said sure, it’s a legitimate expense. Whether or not pictures of the bunnies were attached to his tax returns is still unknown. Haha!