Kapil Sharma is the comedy genius from India who captured millions of hearts with the relatable humor and quick wit. The ‘woke’ culture and increased sensitivity of social media, though, have introduced unprecedented pressures on comedians around the world. In this light, the author explores an inspiring journey from humble origins to stardom while addressing the constraints imposed by evolving audience sensitivities of Kapil Sharma. Highlighting controversies such as jokes on mental health, it looks at the delicate balance between humour and cultural awareness. Using insight into the mental cost of public backlash and changes in the norms of comedy, the piece underlines Sharma’s adaptability and resilience in redefining comedy in a socially conscious era.