Mehboob was born in Mattancherry, Kingdom of Cochin, into a family beset with stark poverty. He spent his childhood in the nearby Bengal battalion military camppolishing shoes while his mother did cleaning jobs. At the camp Mehboob picked up different languages and songs from soldiers drawn from various parts of the country, some Britishers too. Mehboob grew up to become the singer of choice for the various pre-nuptial ceremonies conducted by rich families in Cochin. He made his name, friends and admirers from here. Mehboob had no real home, but he lived with his friends. Many of his early songs were written by Mepalli Balan and Nelson Fernandes, with that special Mattancherry flavour. These songs were never recorded. It was Pankaj Mullick who recognised Mehboob's singing ability for the first time. He recommended Mehboob for several "Kacheris" and Mohammed Rafi concerts. Mehboob became quite famous throughout Cochin in late 1940s itself. Cochin based actor Muthiah recommended Mehboob to music directorDakshinamoorthy, who was looking for a new voice for the film Jeevitha Nouka. Mehboob recorded three songs including the popular "Akaale Aarum Kaividum" for this film, widely known to be the first superhit film in Malayalam. With the success of this song, Mehboob was shot to fame and became the most sought after singer of that time. In 1954, he recorded "Manennum Vilikkila", for the landmark film Neelakkuyil, which became a tremendous success. He went on to record numerous hit songs for composers M. S. Baburaj, K. Raghavan, G. Devarajan, R. K. Shekhar and many more. Most of his songs were folk music based comic numbers and had lyrics by P. Bhaskaran. Mehboob has also recorded numerous songs for stage plays, gramaphone records and other programmes, which is perhaps many times more than he recorded for films. He was also an inevitable performer in "Mehfils" and other concerts. Mehboob was never a careerist. He was known to be an alcoholic and finally died nearly an impoverished man, aged 56. Many of his songs were remixed and used in later Malayalam films. A part of the song "Theerchaayilla Janam", written by Kannan Pareekutty and sung in 1956, was rendered by actor Mohanlal for the 1999 filmUsthaad. The 2013 film Annayum Rasoolum used the songs "Kandu Randu Kannu" and "Kayalinarike". The 2013 film featured the song "Nayapaisayilla" from the film Neelisally.