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.

Dan Penn – $1 Million