He's actually an inspiration to all those who may be despairing in their endeavors. Kristofferson was offered a position to teach English Literature at West Point in 1965, when he was 29 years old. He decided to reject that, and instead to pursue songwriting and singing. His family disowned him for his decision and they never reconciled. He was destitute because of his son's medical expenses and ended up divorced. He showed up in Nashville trying to get singing work, and instead he became a janitor at Columbia studios. He sold a couple of songs to Johnny Cash while sweeping floors. While he was sweeping the floors there, Dylan recorded Blonde on Blonde. Kristofferson never met Dylan there, though, because he was afraid he'd be fired. He had another job flying a helicopter for a private company, and he got Johnny Cash's attention by landing the copter in Johnny Cash's yard and handing Cash some demo tapes.

After that time, he went on to sell some songs, and made some successful albums and eventually became a very successful songwriter, singer, and also an actor and director. He dated Janis Joplin and Barbara Streisand, among others.
It just goes to show -- one can go from destitute to the top of the heap. Kristofferson wrote Me and Bobby McGee, which is one of the most famous songs Janis Joplin did. He also wrote Sunday Morning Coming Down, which Johnny Cash made famous.
- Kris KristoffersonFreedom is just another word: It seems to get truer the older I get. It makes me think about the time when my apartment got robbed and everything was gone and I was disowned by my family. I owed money to a hospital and I owed my wife five hundred a month for child support and I thought, "I'm losing my job." I hadn't any money, I hadn't anything going for me, but it was liberating. I was in this Evangeline Motel, like something out of "Psycho", a filthy place, just sitting there with this neon Jesus outside the door, in the swamps outside of Lafayette, Louisiana, and I thought, "Fuck. I'm on the bottom, can't go any lower" -- and from then on, man, I drove my car to the airport, left it there, and never went back to get it. Went to Nashville and called this friend of mine, Mickey Newberry, and told him I'd just got fired, and he said, "Great. Johnny Cash is shooting a new TV show. Come up, and we can pitch him some songs." The next moment, they cut three of my songs, and they were hits. I never had to go back to work again.
So, who else is an inspiration?