In 2000, he wrote a widely-disseminated piece in Rolling Stone about the origin of the song "The Lion Sleeps Tonight", tracing its history from its first recording by Solomon Linda, a penniless Zulu singer, through its adoption by The Weavers, The Tokens and many of the folksingers of the 1960s, and its appropriation by The Walt Disney Company in the movie The Lion King.
From the late '50's until his semi-retirement in 1990, he arranged music for Nina Simone (1967), Al Hirt, Benny Goodman, Connie Francis, Sam Cooke, The Softones, The Tokens, The Platters, Brook Benton, Sylvia, Ray, Goodman & Brown, Cameo, Little Peggy March, Della Reese, Panama Francis and Pat Thomas among others.
After leaving the Tokens, Medress co-produced (with Dave Appell) many of Tony Orlando and Dawn's hits as well as Melissa Manchester's LP.
The Tokens shopped "He's So Fine" to ten labels before placing it with Laurie Records.