Amedeo Modigliani (July 12, 1884 – January 24, 1920)

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Portrait of a Young Girl
1915

One of the most noted Expressionists, Modigliani, in my opinion, painted some of the most jarring and uncomfortable portraits you can lay eyes on. Still absolutely beautiful and, if you'll pardon the apt cliche, haunting paintings. 

Portrait of Frank Burty Haviland
1914

Portrait of Diego Rivera
1914

The Beggar of Leghorn
1909