[5] Noted for his expert mimicry and mastery of dialects,[7] Cleary initially employed the standard "Jewface" portrayal of that era as his signature routine.
"[16] On April 20, 1942, Cleary appeared in Lux Radio Theatre's adaptation of the 1941, Oscar-nominated biographical drama, One Foot in Heaven, portraying Preston Thurston, the part played by Gene Lockhart in the film.
[23][24] Notwithstanding a film career confined strictly to small supporting roles, the lion's share uncredited, Cleary did manage, in at least two of the four films in which he received an onscreen credit, to elicit reviewers' acknowledgement of his good work; namely, the 1950 prison drama, State Penitentiary, in which he doubles as the Warden and Narrator, and the 1952 baseball biopic, The Pride of St. Louis, in which Cleary portrays Ed Monroe, Dizzy Dean's minor league manager.
The latter had a brief acting career of his own during the late 1940s and early 50s, most notably with a substantial role in both the original Broadway run and subsequent tour of Stalag 17.
[35] As of January 1920, and continuing through at least May of that year, Cleary owned the company, Leo's Auto Painting Shop, offering "first class work" and "moderate prices".