Initially planning to perform antimilitarist pieces by Paul Scheerbart in a men's suit, Waldoff had greater success with less offensive catchy songs written by Walter Kollo.

She was known for singing her songs in distinctive Berliner slang, attired in a shirt with a tie and the fashionable crop hairstyle, cursing and smoking cigarettes on stage.

From 1924 she performed at the two great Berlin varieté theatres, Scala and Wintergarten, sang together with young Marlene Dietrich, and had her songs played on the radio as well as released on record.

During the Great Depression in 1932, Waldoff performed in an event hosted by the Communist Rote Hilfe organization at the Berlin Sportpalast, which earned her a temporary professional ban (Berufsverbot) when the Nazis and Hitler came to power the next year.

After she joined the Reichskulturkammer association the ban was lifted, but Propaganda Minister Joseph Goebbels continued to regard her with suspicion because her manners and appearance contradicted the official role model of women in Nazi Germany.

In World War II she made last appearances in Wunschkonzert broadcasts of the Großdeutscher Rundfunk and in Wehrmacht troop entertainment shows.