He was a member of the American Institute of Architects and the Art Students League of New York, as well as the Society of Independent Artists and the Royal Academy.
He created the scenery for a Nora Bayes show in 1916,[7] and designed the sets for the Jerome Kern / Guy Bolton / P.G.
[10] Cobb was also identified as creating the sets for Ruth Comfort Mitchell's "The Sweetmeat Game" which starred Olive Wyndham and ran at the Palace Theater in November 1916.
In May 1929, Cobb gave a lecture on "the Practical Aspects of Interior Architecture" at Kauffman's department store in Philadelphia.
He was identified in the advertisement as the "son of the illustrious architect who designed the beautiful Gothic buildings on the University of Chicago campus, a Beaux Arts man, and a member of the Royal Academy of Munich."
[16] When his father died in 1931,[17] Cobb Jr. closed the architecture firm almost immediately to "pursue the elusive muse of painting.
He worked primarily in oil and gouache, although he also created many political cartoons, some indicating opposition to The New Deal,[20] in charcoal.
[21] In 1933 and 1934, James Newlin Price held shows of Cobb's paintings at his Ferargil Galleries at 63 East 57th Street, New York.
[25] He commonly signed his oil paintings "HIC," and his gouache works with a block-printed "Henry Ives Cobb," only once or twice adding "II" or "Jr." to the signature.
Mrs. Cobb subsequently moved to England and with her partner Norman Webb ran the Easton Park Hotel in Chagford, Devon, where Evelyn Waugh wrote much of Brideshead Revisited.
[31] Mrs. Lynes donated Cobb's collection of John LaFarge's sketches and renderings to Columbia University, where they can be found in the Avery Architectural and Fine Arts Library.