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One lost early film "Starvation Hunters"dampened his career. He donned a short fat mustache and a derby hat. His resemblance to Charlie Chaplin did not help him at all; Hollywood had room for only one Chaplin, and he never wore that same mustache again.
Sinclair is most famous for his stunt doubling for W.C. Fields. In one of Fields' lost silent comedies, "Two Flaming Youths", Sinclair saved Fields' life.
Fields was supposed to ride a bicycle up the ramp of a slowly backing up truck. Fields looked away, misjudged his approach, missed the ramp and banged his head on the undercarriage of the truck. Fields reported that he knew the truck was still rolling, but couldn't move his body out of the way. His neck was broken. Everyone on the set started screaming at the truck driver to stop, but he didn't hear them, and Sinclair dived to the ground and pulled Fields out of the way of the approaching wheels.
His quick actions guaranteed him work in the future with Fields. Working with Fields was difficult. Writing for Fields was impossible. Fields hated writers. However, if one of his crew ever offered up a good gag while preparing to film, Fields would walk over to that person and hand him a hundred dollar bill. This is how Sinclair became a gag writer for Fields. The most famous movies Sinclair wrote gags for were "It's a Gift"and "Man on the Flying Trapeze" although he contributed to more movies, but again gag writers were mostly anonymous during this period of film history.
Sinclair, like Fields, loved his drink. One would think that because of their working relationship and similar "hobby," that the two would have been good friends, however, as much as Fields loved to drink, he hated drunks. Sinclair, sadly, was a drunk.
Around 1930, Sinclair married one of Mack Sennet's bathing beauties, as well as an up and coming comedy star, Thelma Hill. Sadly, alcohol too would be Hill's downfall.
Within two years Hill would leave movies to become Sinclair's housewife and drinking partner.
In 1932 Sinclair got the role of Secretary of Labor in W. C. Fields' "Million Dollar Legs"." He had one line and one stunt he did standing in for Fields. You can spot when Sinclair stands in because his hair is darker than Fields and Sinclair had a bit of side burns, whereas Fields did not.
His next role, quite short, was as a heavy in the movie "High Gear". But the one movie everyone remembers him in was his next: W. C. Fields' "The Barber Shop". Sinclair was the poor sap, Mr Flugg, who got the shave. Sinclair also does the one stunt at the end of the film, when Fields, riding a bicycle, falls down the stairs, and the bad guy tumbles after him falling on top.
Sinclair wasn't quite as tall as Fields. To make them equal in height, Fields wore shoes without heels, and Sinclair wore shoes with a slightly taller than usual heel. You can spot the heels as he gets into the barber chair, but they're even more prominent in the fall he takes. Before the switch, when Sinclair is on the floor to where they cut and then Fields is on the floor, you can see Sinclair's heels; after the cut, you can see that Fields wears no heels. In this scene, Sinclair also wears a plastic W. C. Fields mask.
In "Poppy", Sinclair wore that mask too, only this time it was for about 75% of Fields' scenes, mostly long shots. Fields was very ill during this period, so ill that it's been said he gave up drinking for about a year, though others have said he gave it up after the death of a friend who had died from drink. In addition to his illness, Fields had trouble with his equilibrium. Every few feet of walking he'd fall over. This happened so often that the director placed people on the ground along his path to catch him when he fell.
In one scene where Fields was to come through a window, then hide under the sink because he heard someone enter the home. When the coast was clear, he was to crawl out. During rehearsals, he tried again and again to get out from under the sink but failed. The director finally said, "Bill, let Sinclair do it. He's an old plumber and knows how it's done." To which Sinclair responded graciously, "Sure, I never really feel at ease anywhere else."
Though it was kept quiet in Hollywood, Southerland, the director, admitted later that Sinclair was in nearly every shot except for the close-ups saying, "I don't think Willie was in 25% of this picture."
Sinclair buried his wife, Thelma Hill in 1938. She had died from complications of chronic alcoholism. This did not stop Sinclair's drinking. He moved from his home, which was just minutes from the Mack Sennett studios to an apartment on the corner of W Jefferson Blvd and 7th Ave in Los Angeles. He remarried, but it wasn't a happy marriage. The jobs came slowly, his movie career started to falter, his parts were still small and uncredited, and worst of all, he fell out of favor with W. C. Fields, David Sharpe having taken his place as Fields' stunt double.
The last we hear about Sinclair is from a short write-up in "Variety" Feb 13, 1943, about his being hospitalized with head wounds and his new wife, Vivian, being held on charges of assault.
Sinclair died on February 13, 1945 of cirrhosis of the liver, at the age of 45. He is buried at Pierce Brothers Valhalla Memorial Park, in North Hollywood in a grave marked only by a brass plate with nothing engraved upon it.