During his sophomore year Benjamin enrolled in a new class offered by Colonel Thomas Humes Williamson, professor of architecture and drawing. The young artist flourished under Williamson’s direction and discovered the passion which would define his career. Clinedinst decided to leave VMI and continue his education at the Maryland Institute of Art with noted landscape painter Hugh Newell.

Frederick Dielman, an influential New York City based professor of art, encouraged Clinedinst to study abroad. Arriving at the Ecole des Beaux Arts in 1881, he became a student of the academic artist Alexandre Cabanel. In 1884, Benjamin successfully exhibited in the Paris Salon.

Clinedinst returned to the United States in 1885 and moved to Baltimore where his father had established a photography studio. He supported himself by teaching at the Charcoal Club and as an illustrator for several prominent magazines of the time. Clinedinst’s painting interest focused on portraiture, genre scenes and depictions of moments from American history.

In 1888 he married Emily Waters. The couple moved to New York City where Clinedinst was employed as an instructor at the Gotham Art School. In 1889 he began exhibiting at the National Academy of Design and, in 1898, was made a full Academician. A founder of the Society of Illustrators, Benjamin was awarded the Evans Prize by the American Watercolor Society in 1899.

In 1900 he replaced Howard Pyle as the Director of Illustration at Drexel Institute, Philadelphia, and filled a similar position at Cooper Union, New York City.

During the last quarter of the 19th century, Clinedinst worked for Leslie’s Weekly, Scribner's and Century magazines. He illustrated books for Nathaniel Hawthorne, Harriet Beecher Stowe, Thomas Nelson Page and Mark Twain, among others. His portrait subjects include Theodore Roosevelt and Mark Twain. Benjamin West Clinedinst and his family moved to Pawling, New York in 1905 where he lived and worked until his death in 1931.