In 1918 Helmut Kolle met his business partner, lover, and mentor Wilhelm Uhde, an art collector, and moved with him to Weimar.

After early experiences as a fledgling writer, Kolle shifted his focus more and more to painting, getting instruction from Erna Pinner in 1918/19, made possible by Uhde's connections in the art world.

At a 1926 exhibition, almost all paintings shown were also sold, and around this time Helmut Kolle began signing his paintings as "Kolle" instead of using his earlier pseudonym "Helmut vom Hügel" (which is a complex pun based on the fact that the Latin word colle, which sounds like Kolle, is the ablative of collis, "hill", and can mean "from the hill" when combined with an appropriate preposition—which then translates back to German as vom Hügel).

[9] Kolle's works, insofar as they depict people, tend to feature either males, often in various states of undress or slightly suggestive poses, either (in his earlier works) very feminine-looking boys or (later in his career) decidedly muscular men, the shift probably influenced by the ideals of masculinity as found in novels by Henry de Montherlant.

]: Helmut Kolle – Ein Deutscher in Paris (exhibition catalog), 2010, 297 pp.