As a child, he worked in Bombay films like Kismet. He later had a number of odd jobs, selling poultry
products and working as a driver for director P. L. Santoshi. Santoshi's son, Rajkumar Santoshi, would
later cast him in the film Andaz Apna Apna (1994). Many of Mehmood's film songs were sung by Manna Dey.
Mehmood reportedly taught table tennis to actress Meena Kumari. After marrying legendary actress Meena
Kumari's younger sister Madhu in the early 1950s and becoming a father by having a son, Masood, he decided
to act to earn a better living starting with a small break as a killer in the film C.I.D. (1956 film). He
started off by doing small, unnoticed roles in films like the peanut seller in Do Bigha Zameen and Pyaasa.
He later went on to act in lead roles as well, but he was more appreciated for his comedy, some of which
was in the Hyderabad region's Urdu accent. Mehmood knew exactly how to tickle the film viewers' funny
bone. He was really good at playing the film hero's friend, who would help him out of sticky situations
with his street-smart ways.
Besides actress Shubha Khote, he also teamed up with fellow comedian, I. S. Johar and actress Aruna Irani