Kris Kristofferson wasn’t just a legendary songwriting talent, and he wasn’t just a multi-faceted star of stage, page and screen. He also just might be one of country music’s most fascinating people ever.

As the country music world grieves his death (Sept. 28), many stars are remembering Kristofferson for his kind, generous spirit, his luminous live presence or his many contributions to the country music songbook.

But Kristofferson was also a man who lived an extraordinary, eventful life with more than its fair share of lore. Some of his craziest stories are so incredible, it’s tough to say whether they happened at all — or whether the people involved have embellished them a little bit in the retelling.

Still, there are plenty of Kristofferson stories that are downright true, and downright wild.

Need proof? Let’s look back to the time he gave up a prestigious military career to be a janitor, or the time he landed a helicopter in Johnny Cash‘s front yard — and don’t forget the time he sang a duet with Miss Piggy!

While Kristofferson has left an indelible mark on country music through his songs and films, over the course of his career, he also stood out as one of the genre’s undeniable, original bada–es.

Scroll through the gallery below for a round-up of Kristofferson’s most unforgettable stories through the years.