Tom Waits – $25 million
Greatest Hits: Closing Time, Somewhere
Tom Waits, born in California, is a singer-songwriter and actor. He is recognized for his distinctive style and his lyrics containing heavy punk elements. He focused on jazz, but he also had blues and vaudeville influences. The Beat Generation and Bob Dylan inspired him. He signed an asylum agreement in San Diego and moved to Los Angeles. His first albums, which marked his first commercially successful album, included Closing Time, Saturday Night’s Heart, and Small Change.
Dan Penn – $1 million
Greatest Hits: Cry Like a Baby, The Dark End of the Street
Dan Penn is a successful songwriter who wrote and recorded The Dark End of the Street, Cry Like a Baby, and Do Right Woman hits from the 1960s. Numerous other artists, including Spooner Oldham, collaborated with Penn. As he was camera-shy, he preferred songwriting over showmanship. The composer’s relationship with Chips Moman was successful, although the pair had a fall-out that ended the relationship, defined as “short-lived” but “intense.” One of his most successful collaborations to date is his collaboration with Aretha Franklin.