In 1911, Wassily Kandinsky and Franz Marc invited Albert Bloch to exhibit with their newly formed group of vanguard artists working in Germany, Der Blaue Reiter. Bloch earned the distinction of being the only American to participate in their landmark exhibition held later that year. Painted around this time, Portrait of a Long-Haired Man belongs to a small body of work that survived Bloch’s Munich period—many works were destroyed during both world wars—and reflects the artist assimilating new ideas. His portrayal of the figure recalls his previous career as a caricaturist and illustrator in his hometown of St. Louis as seen in the figure’s droopy blue eyes, elongated red nose, and severe blunt haircut. The directness of approach, with bold areas of color and expressive brushwork, illustrates a shift in technique, and has been linked to the influence of Van Gogh, whose work Bloch observed on a trip to Paris in 1910 (Henry Adams et al., Albert Bloch: The American Blue Rider, 1997, pp. 25, 57).