I’m feeling sorry for myself-so I need a pick me up. I always liked stories about people who went from poverty to riches and back again.
The one I most remember is William C. Durant (founder of GM). He started out as an office boy, rose to the head of Durant-Dort, and founded GM. he then went broke, and died in a walk-up apartment above a bowling alley (which he was managing). Even at the end, he had big dreams ( he was planning a nation-wide chain of bowling alleys).
Any recommendations?
Try Carl Fisher
Horace Tabor - Wikipedia and Baby Doe Tabor
The Reverend Billy Sunday.
Not seeing where he lost his riches.
Didn’t realize this was limited to rags-to-riches-to-rags. My bad.
ralph does have a habit of messing up his thread titles.
If you’re counting entertainment, there are many examples:
If you’d like something fictional, try “The Jerk” with Steve Martin. (I think?)
Psst… see post #9. 
It’s not really rags to riches to rags (I guess in any way, shape, or form), but Howard Hughes certainly built a vast empire (not starting from nothing, though) while becoming a broken, old, lost man at the end of his life. Might be worth checking out.
Two recent examples. Halsey Minor, who founded Cnet and co-founded Salesforce.com and John McAfee, who founded the anti-virus company that bears his name. His fortune was about $100 million at its peak but dwindled to “only” about $4 million later. One of his mistakes was investing in bonds issued by Lehman Brothers.
John McAfee is also completely bonkers.
You gotta love good ol’ MC Hammer. He went from a net worth of $33 million to -$13 million in the space of a couple years.
Irving Berlin. Best rags-to-riches story of all times.
Yeah, but read the OP (rags-riches-rags).
AFAIK, Irving didn’t lose all his dough and end up playing ragtime piano for tips.
That would have been one helluva show, even if all the songs would have been in the key of C 