He began his career on the stage before working for director Thomas H. Ince as a film extra in silent shorts I'm December 1912.

Ray's breakthrough role came in 1915 when he co-starred opposite Frank Keenan in one of his first full-length feature, the historical American Civil War drama The Coward.

[2] Ray's popularity grew after appearing in a series of light silent comedy features which cast him in juvenile roles, primarily young, wholesome hicks or naive, unsophisticated "country bumpkins" that foiled the plans of thieves or con men and won the heart of his dream girl.

In 1920, he abruptly left Paramount after studio head Adolph Zukor refused to give him a substantial pay raise.

[9] By the time Ray signed with United Artists, he had grown tired of playing country bumpkin and juvenile characters in comedy films.

[3][10] In an effort to change his image to that of a romantic leading man, Ray chose to produce an epic historical drama film based on The Courtship of Miles Standish, an 1858 narrative poem by Henry Wadsworth Longfellow.

[11] The poem centers around a love triangle between early American settlers John Alden, Miles Standish, and Priscilla Mullens.

: A Serio-Comic Tale Of Hollywood, screenwriter Frances Marion wrote that numerous people attempted to dissuade Ray from making the film because lengthy costume dramas were not box office draws at the time.

[13] Ray chose not to listen to the advice and, after failing to secure financial backing from a major studio, he put up $500,000 (approximately $8,941,000 today) of his own money to finance the film.

In addition to the $65,000 (approximately $1,162,000 today) 180-ton replica of the Mayflower that was set on a mechanism to simulate it being on rough seas, Ray also had full sized log cabins built solely for exterior shots.

In December 1925, Ray was forced to file for bankruptcy after being sued by more than a dozen creditors for monies owed and back taxes.

[17][21] The day before Ray was to file for bankruptcy, the couple held a dinner party with a personal butler for each of their guests at their home that reportedly cost $30,000.

The magazine featured a mixture of humorous stories and jokes, film reviews and industry news and editorials and articles written by actors and directors including Melvyn Douglas, Groucho Marx and Cecil B. DeMille.

He ended his career in uncredited bit roles in Slightly Dangerous (1943) and An American Romance, which was released a year after his death.