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Ludvig Oskar was the same age as the first generation of Estonian modernists: he was four years older than Konrad Mägi. Nevertheless, his art was never modernist, but was founded on values that are considered classical. He began his art studies at Ants Laikmaa’s studio at the age of 29. His next tutor was Paul Raud, after which he went to the Anton Ažbe Art School in Munich and studied also at the studios of other local art teachers. Oskar also travelled to Italy and Düsseldorf, then again to Munich, and finally to Paris, constantly taking art lessons from various artists.
Back in Estonia, he began teaching art himself, and established, among other things, the Long Leg Gate Tower art studios in Tallinn, which would be used by artists for years to come. In 1944, Oskar fled to Germany, where he passed away seven years later. He was mainly known as a landscape painter.