Though he was the youngest, Jordan was the first of the boys who made up the Dead End Kids to work in films with a role in a 1933 Universal short. In 1935, he became one of the original Dead End Kids by winning the role of Angel in Sydney Kingsley's Broadway drama Dead End about life in the slums of the east side of New York City. The play was performed at the Belasco Theatre and ran for three years with over 600 performances. He appeared for the first season and the beginning of the second but left in mid-November 1936. He returned in time to join the others in 1937 in Hollywood, California to make the movie version of the play, starring big names such as Humphrey Bogart, Joel McCrea, Sylvia Sidney, and Claire Trevor.

Following the making of Dead End, Jordan found himself "released" from his contract at Goldwyn, and, subsequently, he appeared at Warner Brothers with the rest of the Dead End Kids. After one year, Warners released most of them, but kept Leo Gorcey and Jordan as solo performers. Jordan appeared (as "Douglas Fairbanks Rosenbloom") in Warner's Damon Runyon comedy A Slight Case of Murder (1938) and at Metro-Goldwyn-Mayer in Young Tom Edison (1940).