Herbert's earliest movies, like Wheeler & Woolsey's feature "Hook, Line and Sinker" (1930), cast him in generic comedy roles that could have been taken by any comedian. He developed his own unique screen personality, complete with a silly giggle, and this new character caught on quickly. He was frequently featured in Warner Brothers films of the 1930s, including "Bureau of Missing Persons", "Footlight Parade" (both 1933), "Dames", "Fog Over Frisco", "Fashions of 1934" (all 1934), and "Gold Diggers of 1935" (1935), as well as "A Midsummer Night's Dream" (also 1935), a film adaptation of Shakespeare's play. He played leads in "B comedies", notably "Sh! The Octopus" (1937), a comedy-mystery featuring an exceptional unmasking of the culprit.