Seymour Simons returned to Detroit after service in WWI and built a reputation as a pianist and songwriter, providing material for stage stars Nora Bayes and Elsie Janis. In 1919 he wrote “Just Like A Gypsy” with Bayes, who, in addition to being a popular entertainer, was already a songwriter best known for “Shine on Harvest Moon,” written with her performer/husband Jack Norworth in 1910. “Just Like a Gypsy” was recorded in 1941 by Maxine Sullivan and in 1946 by Peggy Lee.

A collaboration in 1926 with Richard Whiting produced “Hello, Baby,” recorded by Ruth Etting, and the popular “Breezin’ Along With the Breeze,” in conjunction with Haven Gillespie, which was first recorded by Josephine Baker, used in the film Pete Kelly's Blues (1955), and sung by Lucille Ball and Desi Arnaz in their 1954 film, The Long, Long Trailer. The trio also collaborated on “(I’m in Love with You) Honey” (1928) which appeared in the film, Her Highness and the Bellboy (1945). With Gus Kahn, Simons wrote “Just Can’t Be Bothered with Me” (1929) and “Sweetheart of My Student Days” (1930).