Human skulls. A helicopter ride to work. Jail time. A llama for a photo shoot. For the past five years, The Certify Craziest Expenses Survey has examined the wackier side of business travel and expense. This year, we look back to the survey’s beginnings in 2013 to pull together our “best of” list to showcase five years of expensing mayhem. After reading this infographic you may ask yourself, “Would we catch these wild expense items, and would they be approved at our company?!” And rightfully so, as some of the purchases are downright outrageous, while others make a lot of sense when the employee adds context. Context is a vital ingredient in the expense reporting process. It adds empathy by giving employees an opportunity to provide reasons as to why and how the expense was a value-add for the organization. This two-way communication between traveler and approver can significantly improve employee happiness—something we deeply value here at Certify. Here are our favorite craziest expenses from the past five years.