Objective: At present there is a deficit of 30-40 % medical teachers in the existing 345 medical colleges in India. This study was done to find out the percentage of medical students who desire to opt for medical teaching, the subjects chosen for their future career and the major factors which influence their decision making were assessed to explore the possible causes of dearth of medical teachers in some specialities. Settings and Design: The study was a cross sectional observational study, done among the medical students and junior doctors in IPGME andR , Kolkata. Methods and Material: A cross sectional questionnaire based study was done on students, interns and house officers of Institute of Post Graduate Medical Education and Research, Kolkata. The answers were treated as confidential and their views and opinions were analyzed statistically. Data obtained was analysed and presented in counts and percentages and chi square test or Fisher__ampersandsignrsquo;s Exact Probability test as applicable. Results: Data collected revealed that out of 149 medicos, 146 (97.99%) were willing to do post-graduation, 3 (2.01%) were undecided; 61(40.9%) wanted to opt for medical teaching, 47 (31.58 %) did not while 41 (27.52 %) were undecided. Regarding the subjects chosen for post-graduation, Surgery, Medicine and Pediatrics held the priority followed by Orthopedics and GandO. Pre and para-clinical subjects were chosen by 4.02%. 132 wanted pre-PG subject counseling. The major drawbacks of the present medical education system were found to be, lack of exposure to clinics in pre and para-clinical subjects, inadequate teaching infrastructure and students not reciprocating the contributions of a teacher. Conclusions: Various factors influence the ultimate career choice of medical students. Exploring and sorting out the deterring factors which hold them back from medical teaching specially the dearth subjects could perhaps help to tide over the present crisis of dearth of teachers.