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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).
In 1940, Jordan appeared in the film Military Academy and accepted an offer from producer Sam Katzman to star in a new tough-kid series called "The East Side Kids.
" Leo Gorcey soon joined him, then Huntz Hall, and the trio continued to lead the series through 1943, when Jordan entered the United States Army during World War II as a foot soldier in the 97th Infantry Division.
He was subsequently involved in an elevator accident, when the elevator fell five floors, that forced him to have surgery to remove his right kneecap.
Sach just lost his job as an assistant to a private detective, but he wasn't paid. Slip goes with him down to the detective's office to demand payment, but finds the office empty. A woman enters the office and mistakes Slip for the detective and convinces him to take on a case to find her sister after offering a $50 retainer.
The Bowery Boys--Slip, Sach, Bobby, Whitey & Chuck--start their own exterminating service, and get a job which takes them to a spooky old abandoned mansion in the middle of the night. Meeting up with pal Gabe and his new French bride, the boys are tormented by mad scientists who try to convince them the place is haunted and then kidnap Sach in order to place his brain inside a gorilla.
Slip (Leo Gorcey), Sach (Huntz Hall), Bobby (Bobby Jordan), Whitey (William Benedict) and Chuck (David Gorcey) unsuccessfully try to sell a dilapidated car to a street cleaner for a fabulous amount, so they can get enough money to save Louie's (Bernard Gorcey) Malt Shop. Sidewalk photographer Cathy Smith (Teala Loring) snaps a pictures of three bank robbers as they are fleeing a robbery but when the Bowery Boys and Cathy realize that Sach is also in the photograph, they break into the photo lab to destroy the negative, which might make the police think Sach was involved in the robbery.
Flagwaving story of a new American destroyer, the JOHN PAUL JONES, from the day her keel is laid, to what was very nearly her last voyage. Among the crew, is Steve Boleslavski, a shipyard welder that helped build her, who reenlists, with his old rank of Chief bosuns mate. After failing her sea trials, she is assigned to the mail run, until caught up in a disparate battle with a Japanese sub. After getting torpedoed, and on the verge of sinking, the Captain, and crew hatch a plan to try and save the ship, and destroy the sub.
Muggs' rich Uncle Pete is coming to visit. Unfortunately, Muggs' late father had bragged that he had seven kids, so Muggs recruits the members of the gang to pose as his family. Things turn sour, however, when a local mobster finds out about Muggs' deception and threatens to expose it.
The gang is sent to the Wilton Reform School after they are unjustly convicted of stealing a truck. Bill Collins, brother of co-leader Danny, becomes involved in a killing and, while also innocent, is convicted and sentenced to death. Through a series of events, Muggs, Glimpy, Danny and the rest of the gang, learn that Knobby, a henchman of Luke Manning, knows something about the murder.
Inventor Thomas Edison's boyhood is chronicled and shows him as a lad whose early inventions and scientific experiments usually end up causing disastrous results. As a result, the towns folk all think Tom is crazy, and creating a strained relationship between Tom and his father. Tom's only solace is his understanding mother who believes he's headed to do great things.
A young man just released from a reformatory moves to a new neighborhood with his sister, intending to start a new life. However, he gets mixed up with the local mob boss and corrupt politicians and soon finds himself being framed for an arson and murder he didn't commit.
In the slums, teenager Frankie Warren hangs out with a rowdy gang who one day knock him out in a fight. In court, the boys refuse to reveal who struck the knockout blow, and all are subsequently sentenced to a reformatory, cruelly run by two corrupt guards. New deputy commissioner Mark Braden arrives determined to change things, but despite the help of Frankie's sister, Mark's reform plans -- and Frankie's future -- may be sabotaged from within.
Mobster "Baby Face" Martin returns home to visit the New York neighborhood where he grew up, dropping in on his mother, who rejects him because of his gangster lifestyle, and his old girlfriend, Francey, now a syphilitic prostitute. Martin also crosses paths with Dave, a childhood friend struggling to make it as an architect, and the Dead End Kids, a gang of young boys roaming the streets of the city's East Side slums.