The communist parties in India were able to withstand the cataclysmic events faced by Marxist parties in many socialist states in the 1990s. Even after the collapse of the former Soviet Union, Marxism-Leninism continues to inspire resistance movements in India. The parliamentary left remains a powerful ideological alternative in three major states – West Bengal, Kerala and Tripura – of federal India. Of all these states, Kerala stands out since this is where the Communist Party of India captured power for the first time in the history of communism through democratic election. Besides resorting to the parliamentary path, the parliamentary left in Kerala has also shown how to run a coalition government comprising the left and left-minded political parties in highly diverse socioeconomic circumstances. This is a unique experiment, showing how an ideology-driven government fulfils its socio-economic mission in a liberal democratic set-up. A look into the history of communism in Kerala points out three major challenges for the left parties forming the conglomeration of the parliamentary left: first, how the communists who were persuaded to pursue a revolutionary path of socio-economic changes adapted to the practices and principles of parliamentary democracy and a multi-party system; second, how the CPI and later CPI (M) defended their ideological faith in class politics within the constraints of coalition politics wherein non-left parties were also occasionally included. The third challenge of left politics in Kerala is how to remain viable in a left political front along with the pluralistic social left, which is a very recent phenomenon. By concentrating on the evolution and functioning of the parliamentary left in Kerala, this chapter is an attempt to identify the possible factors that account for its organic growth in a milieu which was not exactly in its favour. The story that follows aims to draw out the distinctive nature of such an experiment which is both theoretically innovative and intellectually refreshing. The fact that the parliamentary left in Kerala always remains in the reckoning as a powerful political entity unlike its counterpart in West Bengal provokes a further debate when attempts are made to explain the phenomenon in one-sizefits-all format.