Tom Waits – $25 million
Greatest Hits: Closing Time, Somewhere
Tom Waits is a California-born singer-songwriter and actor. His distinctive sound and punk lyrics are renowned. He specialized in jazz in the 1970s but also influenced blues and vaudeville. Generation Beat and Dylan inspired him. He began singing in San Diego, moving to LA for an asylum deal. His first albums included Closing Time, Saturday Night’s Heart, and Small Change, which marked his first successful album.
Dan Penn – $1 million
Greatest Hits: Cry Like a Baby, The Dark End of the Street
Dan Penn is a songwriter who composed and released several songs in the 1960s, including “The Dark End of the Street,” “Cry Like a Baby,” and “Do Right Woman.” Bands such as The Box Tops, Chips Moman, Spooner Oldham all performed together. As camera-shy, he preferred songwriting to showmanship. His writing relationship with Chips Moman for Press Publishing Company was successful, although the pair had a collapse that ended the partnership, defined as “short-lived” but “intense.” His collaboration with Aretha Franklin is one of his most successful collaborations to date.