Singer-Songwriters Who Are Highly Successful Because Of Their Work

Published on 01/08/2021
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Tom Waits – $25 million

Greatest Hits: Closing Time, Somewhere

Tom Waits is a singer-songwriter and also an actor. He’s known for his distinctive, gravely sound and punk lyrics. He specialized in jazz in the 1970s but also had blues and vaudeville influences. Beat Generation and Bob Dylan are his inspirations. He started singing in San Diego and went to LA to sign an asylum deal. He had his first commercially successful album, Closing Time, Saturday Night’s Heart, and Small Change.

Tom Waits

Tom Waits

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Dan Penn – $1 million

Greatest Hits: Cry Like a Baby, The Dark End of the Street

Dan Penn is a songwriter who wrote and recorded a variety of hit pieces in the 1960s, including “The Dark End of the Street,” “The Cry Like A Baby,” and “Do Right Woman.” He preferred to play songwriting because he was camera-shy. For the press release company, his writing relationship with Chips Moman was successful, although the pair had a fall-out that ended the partnership, which was described as “short-lived” but “intense.” His collaboration with Aretha Franklin is one of his most successful since then.

Dan Penn

Dan Penn

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