Enn Põldroos was born in 1933 in Tallinn, graduated from Tallinn State Applied Art Institute of the ESSR in 1958 as a painter and became a member of Estonian Artists' Association in 1959. In addition to being an artist, Põldroos has been politically active for most of his life, he has also been the president of Estonian Artists' Association. The artist has earned Kristjan Raud Art Award three times, he has received the 4th Class Badge of the Order of the National Coat of Arms of Estonia (2002), the 3rd Class Badge of the Order of the National Coat of Arms of Estonia (2006) and Estonian State Cultural Award for lifetime achievements.

There are two main elements in Enn Põldroos' 1960s paintings: depiction of existential dread and spheres or containers as ever-present symbols. At that time, he often juxtaposes human solitude and the simultaneous universality of human sensibility. One ought not to ignore the context of living in a Soviet state either: a place and time when certain tendencies of human nature found a chance to get amplified, and without that context, Põldroos' paintings would not be what they are. His artworks from that era often refer to religion.

The 1970s witness a breakthrough in his artistic work and Põldroos' paintings from the 1980s are totally different from the prior. Canvases drawn and painted diligently from edge to edge compared with traditional shading and color transitions were now replaced by fragmentary forms. One could say that whereas in the 1960s the artist directed all his abstract thought into symbolism, then by the 1980s, in addition to having gone deeper contextually, he had extended his abstract thought onto the form of his paintings. The abstractionism is evident in bold color choices and slightly impressionistic yet more powerful brush strokes. Portraits from the time showcase Põldroos' increased interest in the individual character of whom he's painting. Changes in his attitude towards people and the world are also visible. A viewer who has lived enough could compare Põldroos' paintings from different decades and see a life story there, perhaps something to relate to.

In the 1990s when Estonian society went through major changes and had to invent itself, Põldroos' works, on the contrary, show signs of maturity. Paintings completed in the 1990s and onward carry many elements that the artist had always cared about. These were the topics that had now had time to brew in his mind, and in the 1990s he returned to them, combining them in new ways. The theme of religion, too, has come to Põldroos' paintings, but this time it is met with the technical and formal tools that the artist had only developed in the 1980s. Põldroos has never ceased to be a seeker. One of his latest quests has been contemplating the medium of photography and how to use its symbolic potential in painting.