Friedlander was studying at the Art Students League in New York when he was just twelve years old; at fourteen he was employed as an apprentice in the Klee Brothers shop, craftsmen who made architectural ornament to order. He advanced quickly to the work of direct modeling, and continued at this work until 1908, when he went to Europe, and study at the Ecoles des Beaux-Arts in Paris and in Brussels. Soon after his return to New York in 1911 he won his first major commission, for decorative sculpture for the Valley Forge, Pennsylvania, Memorial Arch, designed by Paul Cret. Two years later, having won a fellowship to the American Academy in Rome, he went to Italy where he remained until 1917.
In the years following World War I, Friedlander worked as assistant to Hermon MacNeil, and to Paul Manship. He also received several independent commissions through Bertram G. Goodhue to execute architectural sculptures for churches Goodhue designed for various clients in the Mid-west. Cass Gilbert employed him to execute twenty-six relief panels for the United States Chamber of Commerce Building in Washington, D. C.
Perhaps the sculptor's most important commission came from McKim, Mead and White in 1929: the creation of two colossal equestrian groups for the Washington, D. C. terminus of the Arlington Memorial Bridge, spanning the Potomac River, linking the Lincoln Memorial and Arlington (Virginia) National Cemetery complexes. (The groups, representing Valor and Sacrifice, were not cast in bronze until 1950, and were dedicated the following year.)
In New York, Friedlander was responsible for the large allegorical reliefs, New Frontiers, installed over the entrances to the RCA Building in Rockefeller Center; for the 1939 World's Fair he executed the colossal Four Freedoms groups (destroyed).
Sculpture of colossal scale was Friedlander's special forte; inevitably a city work space was too confined; he established his studio in White Plains, New York, in 1935.
Friedlander remained an active and vocal artist until the time of his death. Among his later works were a twenty-three foot Archangel and chapel door panels for the American Cemetery at Hamm, Luxembourg, dedicated in 1960; architectural sculptures for the Cathedral of Mary Our Queen, Baltimore, Maryland; and similar work for the Wesley Theological Seminary, Washington, D. C.
Friedlander's sculptures were first seen in Academy exhibitions in 1917, and he continued a regular participant in the exhibitions. He won the Academy's Barnett Prize in the winter exhibition of 1918, and again in the winter exhibition of 1923. During World War II Friedlander taught at the New York University School of Architecture. He was a member of the National Sculpture Society, and its president from 1954 to 1957.