Robert Woolsey, the cigar-chomping, slick-haired, bespectacled member of the Wheeler and Woolsey comedy team, was born in California and raised in Carbondale, IL. After the death of his father, it was up to Woolsey and his brother, Charlie, to support their family. Small and wiry, Woolsey found work as a jockey, but a fall from a horse at age 15 ended his equestrian career. Looking for a less strenuous occupation, he became an actor, playing up to 80 different roles in various regional stock companies. While appearing with the Rorick's Company in upstate New York, he befriended a fellow Californian, comedian Walter Catlett. An admirer of Catlett's brisk, commanding style, Woolsey decided to deliberately pattern himself after Catlett -- right down to the horn-rimmed glasses and ever-present cigar. He finally made it to Broadway in 1919, and for the next decade was gainfully employed as a utility comic in such productions as The Right Girl, The Blue Kitten, and Poppy, co-starring in the last-named production with W.C. Fields.
In 1927, Woolsey was hired by Florenz Ziegfeld to play wheeler-dealer divorce attorney Chick Bean in the Broadway musical spectacular Rio Rita; it was in this production that he was teamed for the first time with a pixie-ish, wavy-haired comedian named Bert Wheeler. When Rio Rita was transferred to film by RKO Radio Pictures in 1929, Wheeler and Woolsey came along for the ride. They scored an immediate hit, and a new Hollywood comedy team was born. Over the next eight years, Wheeler and Woolsey churned out 21 films, many of them -- Diplomaniacs, Hips Hips Hooray, Cockeyed Cavaliers -- among the best and most profitable comedies of the 1930s. Offscreen, Woolsey was admired by co-workers as a studious, hard-working "technician" -- not truly funny in himself, but wise in the ways of getting big laughs. He was also the businessman of the team, feistily badgering RKO for higher salaries and better material throughout his Hollywood career. After teaming with Wheeler, Woolsey appeared as a "single" only once, starring in the 1931 film Everything's Rosie, a blatant (and unsuccessful) rip-off of his earlier Broadway musical Poppy. Woolsey became seriously ill in 1937, but courageously completed two films that year, On Again-Off Again and High Flyers. On August 27, 1937, Robert Woolsey was confined to his bed, where he would spend the remainder of his life; he died 14 months later at the age of 49.
~ Hal Erickson, All Movie Guide