In 1935, Valentine Dudensing signed Avery onto his gallery, which showed established European and American artists like Matisse,
. Being inducted into such a high profile gallery gave Avery financial freedom for the first time in his life––and, in turn, his artistic exploration was catapulted forward. With a guaranteed income, Avery continued to delve into the avant-garde characteristics of his paintings.
Though his sales were slow, critics took to him kindly, and in 1943, an even larger gallery, Paul Rosenberg & Co., brought Avery onto its roster. Rosenberg purchased 50 paintings from Avery every year, which alleviated his financial worry; as a result, he had one of the most prolific years of his career in 1944. Paintings from this time forward forgoed decorative lines and brushy marks, and opted for canvases drenched in luminous, poetic displays of dense color and flattened shapes.
In Sketchers on the Rock (1943), Avery captures two figures perched atop a boulder in an eerily quiet Vermont landscape. The deep lavender sky is broken up with dark blue-green trees, and the sitters, painted in blocks of tans and oranges, blend into the muted greys of the ground. In Blue Trees (1945), Avery harnesses light-grey blues in the foreground, vibrating against the muted green in the background, to show the feeling of a lively, springing landscape. With every new painting, Avery became more significant in the eyes of his peers (though not many collectors followed suit). When the director of the Museum of Modern Art, Alfred H. Barr Jr., asked Rothko who he thought the most important artists of the moment were, he burst into laughter when Rothko named Avery.
A lack of sales would come to haunt Avery after he suffered a heart attack in 1949. The event left him with angina, a chronic chest pain that never subsided. Less than a year later, Rosenberg would viciously drop him from the gallery’s roster, selling his remaining stock of paintings––about 50 of them––to Roy R. Neuberger for a substantially low price, depressing Avery’s market severely.