Babu Kaliprossunno like many a young heir come to a splendid fortune early contracted the disease of extravagance,-indeed the seeds of the disease had been sown earlier-and he died a victim to it-a warning to others similarly circumstances and similarly inclined !
Hindoo Patriot, July25, 1870
It was a serious dichotomy plaguing the ‘Babus’ of the 19th Century Bengal. While leading a dissolute personal life, with the unimaginable wealth acquired from ancestors, and the vast zamindaris, they were also the pillars of the Bengal Renaissancess. Kaliprasanna Singha was the perfect embodiment of a personality who had imbibed the antagonistic spirit of the age.

We can indeed face a wavering scepticism of sorts while dealing with a figure like Kaliprasanna Singha. He passed away at the age of twenty-nine, on 24 July, 1870, at his ancestral home in Jorasanko, Calcutta. While in his obituary the Hindoo Patriot chose to deride him for his extravagant and indulgent lifestyle, several others thought differently. Dinabandhu Mitra (writer of the controversial play Nil Darpan) calls Kaliprasanna a ‘Pundit’, a scholarly person and a philanthropic zamindar, who donated hugely for social causes. Kaliprasanna was also the famed writer of the satirical Hutam Pyanchar Naksha (1862), which took a dig at the nouveau riche of the affluent Calcutta society, who indulged in every possible depravation to amass wealth. Kaliprasanna established many charitable schools and donated substantially to financially distressed educational institutions. He bought a printing press for the Tattwabodhini Sabha, a splinter group of the Brahmo Samaj, helmed by his illustrious neighbour Debendra Nath Tagore. He also donated another one to Sambhu Chandra Mukherjee, for printing the Mukherjee’s Magazine. When the magazine was closed down, the printing press was donated to Girish Chandra Ghosh for the printing of the Bengali magazine. His efforts to conserve the memory of Harish Chandra Mukherjee and his financial contributions to save the Hindoo Patriot from being closed down, can never be forgotten. His donations for the famine in North-West (1861), setting up a charitable dispensary in Chitpur (1865), importing expensive machinery from England for procuring uncontaminated drinking water for the people of Calcutta (1865)-the list is endless. In July 1861, when Reverend James Long was fined Rs 1000/- (a kingly sum in those days), for translating Nil Darpan , Kaliprasanna deposited the entire amount in court himself. He is mostly remembered for his mammoth task of translating the entire Mahabharata into Bengali. He printed three thousand copies of the book and distributed them for free, incurring a cost of 2.5 lakhs of rupees.

Apart from his philanthropic activities, Kaliprasanna performed various other social responsibilities as well. In 1863, he was appointed as the Honorary Magistrate and Justice for Peace. For the years he donated to this job, he attained fame as a very impartial judge. On 3 June, 1865, Sambad Prabhakar wrote :
The Chief Magistrate of the Calcutta Police, Branson Saheb has fallen from his horse and is temporarily indisposed to go to the court. In the circumstances, Babu Kaliprossunno has assumed the responsibilities. It should be known that after the death of Theodore Dickens and in the period before the appointment of Branson Saheb, this Babu had assumed the post of the chief of police and earned praise for his impartial judgement abilities.
Based on his experience, Kaliprasanna wrote a book which was highly praised-The Calcutta Police Act (1866).

To return to the question of dichotomy. The personal life of Kaliprasanna was a disaster. He was born to great wealth, debatably in 1841, to Nandalal Singha of Jorasanko, Calcutta (some records suggest it may have been 1840). His father died when he was six years old. Babu Hara Chandra Ghosh, a judge of the lower court was appointed as his guardian. He was a child prodigy and had the special ability to remember things heard or seen even once. In the perspective, it is not surprising that he formed the Vidyotsahini Sabha in his house, only at the age of fourteen and also the Vidyotsahini Theatre where his plays like Vikramorvashi, Savitri Satyavan, Malati Madhava, were staged for several consecutive years. The last few years of Kaliprasanna were painful to say the least. He married twice but was childless. Despite his philanthropic efforts, he remained a much defiled figure in society. No wonder though, as he had been a student of Hindu College for a while and was quite a Derozian at heart. Rumours abounded of him leading a life against established societal norms. Despite his talents though, he never seemed to possess the talent to manage his huge property. As long as he was a minor and Hara Chandra Ghosh looked after the property, everything was in order. But, when Kaliprasanna assumed responsibility, everything just fell into disarray. He incurred huge debts, was duped by his friends and relatives and was deprived of many of his prized properties, especially the huge zamindari of Orissa and the Bengal Club of Calcutta. He was such a Shelleyesque character in whom patriotism, love for literature and advocacy of justice, simply overshadowed all of his faults. Krishna Das Pal completed his obituary in the Hindoo Patriot by remarking :
But beneath the troubled waters of youth there was a silvery current of geniality, generosity, good-fellowship and high mindedness, which few could behold without admiring. With all his faults Kaliprossunno was a brilliant character and we cannot adequately express our regret that sa career begun under such glowing promises should have come to such an abrupt and unfortunate close.