No.13: Elton John

Global rock icon Elton John was once as famous for his wild spending as for his music. During a 20-month period in the late ’90s, he reportedly burned through £30 million (about $50 million USD), spending over $1 million a month on real estate, artwork, luxury items, and more.

The extravagant lifestyle eventually caught up with him, and by the early 2000s, he was reportedly close to filing for bankruptcy. However, Elton turned things around through lucrative Las Vegas residencies and international tours. Today, he’s back on top—proof that even the biggest spenders can bounce back.
No.12: 50 Cent

Rapper 50 Cent (Curtis Jackson) rose from the streets to superstardom with his debut album, going on to acquire Mike Tyson’s former mansion and build a multi-million-dollar empire.

But after a series of failed business ventures and costly lawsuits, he filed for Chapter 11 bankruptcy in 2015. Rather than hide the move, 50 Cent branded it as a strategic financial decision to restructure his debts. Since then, he has successfully rebuilt his fortune—now estimated at over $40 million—through business ventures in TV, beverages, and music.