[6] Woolsey, who had brown eyes and hair with a slight and slender build[2] tried to capitalize on his size, as a young adult, by becoming a jockey.

Woolsey was teamed with comedy star Bert Wheeler in 1928, for the Broadway musical Rio Rita.

RKO Radio Pictures filmed the play in 1929, launching Wheeler and Woolsey as movie personalities.

Woolsey's comic character was a fast-talking, genially leering, cigar-smoking, wisecracking, and self-confident operator -- but one who was not always as smart as he thought he was.

Ready for any hare-brained scheme, he would often lead Wheeler's more naive, gullible and sweet-natured character into (and only sometimes out of) trouble.