Entertainment | Celebrity Net Worth

Justin Bieber went from living in obscurity in Canada to ruling the airwaves in less than five years. Now he's dangerously close to crossing over from fame to infamy. Here's how a kid from Canada launched an empire, and why he could lose it all.

Seattle rapper Macklemore and his producing partner Ryan Lewis worked hard, believed in themselves, flipped off the system and made a fortune in the process.

Remember the Hong Kong billionaire who offered $65 million to any man who could seduce his daughter out of a lesbian marriage? He's back, and the offer just got sweeter.

How do you become a pop-country superstar? For Taylor Swift it involved isolating herself from other tweens, pouring all of her energy into writing her own tracks, and never taking no for an answer. $150 million and seven Grammy Awards later, her plan seems to have worked.

She is a retired Lt. Colonel in the U.S. army, a celebrated philanthropist and, as of August 2013, James Pritzker is the first transgender billionaire in the world.

When you add up all the events described in Ice Cube's 1993 hit song "It Was a Good Day", you learn that the exact date of his good day had to be January 20th, 1992. Twenty years ago today!

Forever 21 is one of the most successful retail empires in the world today. Along the way, the Korean immigrant founders have earned an insane amount of money. They've also dealt with a few very strange controversies.

There was a time when Seinfeld, the most profitable sitcom of all time, was on television life support. Fortunately for the bank accounts of show creators Jerry Seinfeld and Larry David, destiny had other plans in mind.

There was a time the Saints came within a heartbeat of relocating out New Orleans. Fortunately, Tom Benson saved the day. How'd Tom get rich in the first place?

Becoming an NFL team owner is not an easy task. Who is Stephen Bisciotti how'd he make enough money to purchase the Baltimore Ravens?

Billy Campbell is no longer Allison's whipping boy. In fact, Andrew Shue is all grown up, with enough money to buy Melrose Place, tear it down and tear it down and replace it with a private putting green.

Ozzie and Daniel Silna have agreed to a one time INSANE payout from the NBA which will finally end what has been dubbed "The Greatest Sports Business Deal Of All Time".

Like most multi-billionaire heiresses, after Miuccia Prada graduated from college with a PhD, she went to work as a mime on the streets of Milan. Today she runs a $24 billion fashion empire.

Yoshikazu Tanaka wouldn't have become Japan's youngest billionaire without getting a little help from his Friends..ter.

Shark Tank star Kevin O'Leary, AKA Mr. Wonderful, launched his first business from a basement with a $10,000 loan from his mom. Today he is worth $400 million.