Fine met Shemp Howard and Ted Healy, who were performing in the Shubert Brothers' A Night in Spain. Since Howard was leaving the play for a few months, they asked him to be a replacement "stooge". Fine joined Ted's other stooges, Bobby Pinkus and Sam "Moody" Braun. Howard returned in September 1928 to finish Spain national tour.

In early 1929, Healy signed a contract to perform