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The paintings and sculptures of 34-year-old artist Alex Israel tend to be big, sun-splashed affairs that reflect and refract the sparkly Hollywood demimonde he’s long inhabited. A rapidly rising star, Israel is best known for his self-portraits, done in profile, that reveal a cool-breeze hipster with stubble and sunglasses. In some iterations, he fills in his empty silhouette with Hollywood iconography: directors’ chairs, palm trees, beach scenes.

Israel’s work sells in the high six figures or more—his Sky Backdrop went…