Tom Waits – $25 million
Greatest Hits: Closing Time, Somewhere
Born in California, Tom Waits is a singer-songwriter and actor. His distinctive, heavy sound and punk lyrics are renowned. In the 1970s, he specialized in jazz, but he also had blues and vaudeville influences. The Beat Generation and Bob Dylan inspired him. He began singing in San Diego and moved to LA to sign an asylum deal. His first albums included Closing Time, Saturday Night’s Heart, and Small Change, which marked his first commercially successful album.

Tom Waits – $25 Million
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 several hits in the 1960s, including The Dark End of the Street,” “Cry Like a Baby,” and Do Right Woman.” Artists such as The Box Tops, Chips Moman, Spooner Oldham have collaborated with him. He preferred songwriting, as he was camera-shy, over showmanship. His writing relationship with Chips Moman for Press Publishing Company was successful, although the pair had a fall-out that ended the partnership, defined as “short-lived” but “intense.” His collaboration with Aretha Franklin is one of his most successful collaborations to date.

Dan Penn – $1 Million