Hollander's father was in the fur business, enabling the family to travel to Europe including a nine month stay in Paris. At age 13, he experienced his first adventure with a 1,000 mile bike trip up the Connecticut River Valley alone. He was a memeber of the United States Army's 10th Mountain Division Ski Troops and is a veteran of World War II.
In the mid-20th century, he was a successful filmmaker along with his wife Barbara Hollander before he started painting in 1960, during the abstract expressionism movement in New York City. He became one of the group that defined this movement and whom all hung out at the famous Cedar Tavern. Acrylic paint was just emerging at the time and Hollander was among the first to explore its possibilities. From 1960-1962 he has his studio and the first Hollander Gallery on Bleeker Street, in Greenwich Village. During that time his paintings sold to the likes of Jacqueline Kennedy, Steve McQueen, Norman Rockwell, and Ralph Lauren.
Hollander's work is reflective of his ethos; he makes art because he must, and while he is aware of the art world, it's only vaguely so. His work is honest and emotional; he paints for himself. He has no wish to engage in a dialogue with the viewer. It is for him to paint, for the viewer to view. He refuses to title his paintings. He tells no stories. To him, “there is nothing verbal about a canvas. A painting is simply one way to express a feeling and feelings can only be made less if they are talked to death."