His first figurative paintings began to appear already around 1923-24, during a trip to Zurich, by Hess, and then immediately with the Spanish stay, and they are works alternately marked by an expressionist attitude or by a bright chromaticism, with a dynamic and synthetic sign with smooth and modulated volumes. But already in 1926-27, he lived for a period in Rome, where he made dozens and dozen of drawings from life in the most typical neighborhoods of the city, fixing the most vernacular situations: taverns, street vendors, and so on. The result was a booklet entitled Disegni Romani (Roman Drawings), published in 1927.
Later, towards the end of the 1920s and the beginning of the 1930s, the paintings of German subjects show a sort of coming and going between twentieth-century drives, on the one hand, and an intolerance to neo-classical styles on the other. But this is the Baldessari of the time constantly oscillating between the suggestions that derive from his multiple artistic experiences. Among other things, in Berlin in the early thirties he also worked for cinema, creating various wall posters.