Gary Smith

Luck Run Amok—Part 19

Music and Art Entertainers

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Gary Smith
Aug 25, 2026
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Table 1 shows the wealthiest American musicians. Madonna is the best-selling female recording artist of all time (with 300 million to 400 million records sold) and has been honored for her acting in the movies Desperately Seeking Susan, Evita, and A League of Their Own. Like many other financially successful singers, she has been involved in a variety of businesses including the Maverick entertainment company. The rich get richer.

Dr. Dre and Diddy (also known as Sean John, Puff Daddy, P Diddy, and other variations), made their names famous with hip hop recordings, then branched out into record production and other entrepreneurial ventures. Dr. Dre sold his Beats headphones company to Apple for $3 billion, Combs’ business empire includes a movie production company and a Sean John clothing line.

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