ABSTRACT: The controlled modulation of both oil (under water) and water (in air) wettability is an emerging approach to develop several functional materials for various prospective applications including oil/water separation, anti-corrosive coatings, underwater robotics, protein crystallization, drug delivery, open microfluidics, water harvesting etc. Here, we report a 'reactive' and covalently cross-linked coating through a facile and robust Michael addition reaction, which is suitable for the controlled and extreme regulation of both water and oil wettability in air and under water respectively. Along with extremes (super-philicity and super-phobicity) of water (in air) and oil (under water) wettability, this single multilayer construction was also able to display special liquid wettability (i.e.; extremely liquid repellent-but with controlled adhesive properties) both in air and under water, after strategic post chemical modifications, again through 1,4-conjugate addition reaction. The super-wetting properties in the materials were able to withstand various physical and chemical insults including adhesive tape test, sand drop test, and exposure to extremes of pH, salt, and surfactant contaminated aqueous media. Moreover, this approach also allowed the decoration of various flexible and rigid substrates (i.e.; wood, Al-foil, synthetic fabric etc.) with various bio-inspired wettability properties including (1) non-adhesive superhydrophobicity (lotus leaf), (2) adhesive superhydrophobicity (rose petal), (3) underwater superoleophobicity (fish scale) etc. This single polymeric coating-which is capable of displaying several bio-inspired interfaces both in air and under water, even after harsh physical/chemical insults-would be useful in various prospective and relevant applications for practical scenarios.