Kurt Cobain
Kurt Cobain, the legendary frontman of Nirvana, dropped out of high school just two weeks before graduation. After being kicked out of his parents' house as a teenager, he often slept on friends' couches, but when none were available, he resorted to sleeping under a bridge.
Eventually, Cobain secured a job at a resort, allowing him to rent an apartment. By the time of his passing, his net worth had reached $50 million.
