In 1987, after serving his conscription, Kumar had his first exposure to the entertainment industry at 22 years old as a singing waiter at Cheers! The Fun Pub at the Novotel Orchid. Two years later, he began a stint as an entertainer at Haw Par Villa. In 1991, Kumar landed a gig at the now defunct Laughs Comedy Club in Tanglin Shopping Centre playing the role of an Indian drag queen. It was then when he realized comedy was his calling.