1. Broadcast.com: $5.7 billion
The most expensive and the most important Yahoo acquisition is Broadcast.com. The internet radio company was bought by Yahoo in 1999 for $5.7 billion.
Chris Jaeb was the founder of the internet radio company, which first was AudioNet. But later, the company was owned and led by Todd Wagner and Mark Cuban.
They were the company leaders until April 1999, when Yahoo! offered $5.7 billion for the company.
With this acquisition, Yahoo! stepped into the world of radio, which also helped their revenue grow even bigger.