Loesser's early lyrics included two hit songs of 1934, "Junk Man" and "I Wish I Were Twins" (both with music by Joe Meyer, and the latter with co-lyric credit to Eddie DeLange).
In the mid-1930s he would sing for his suppers at The Back Drop, a night spot on east 52nd Street along with composer Irving Actman, but during the day he worked on the staff of Leo Feist Inc. writing lyrics to Joseph Brandfon's music at $100 a week.