6. Bing Crosby: $550 million
The man who sang “I Haven’t Time to Be A Millionaire” was incredibly wealthy. Crosby ranked among the 10 richest Americans in the 1930s—before he sang “White Christmas” and became one of the biggest movie stars of the ‘40s. His Bing Crosby Enterprises was the first pop artist entertainment empire, with properties ranging from television stations to Ampex magnetic tape technology to horse tracks.
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