Absorption and fluorescence spectra of bicalutamide (BCA) in different solvents and aqueous β-cyclodextrin (β-CD) solutions are reported. The solid inclusion complex of BCA with β-CD is prepared and investigated by FT-IR, 1H NMR, differential scanning colorimetry (DSC) and scanning electron microscopy (SEM). The Stokes shift of BCA is correlated with various solvent polarity scales like E T(30), BK and f(D,n). β-CD studies show that (i) the absorption and emission maxima of BCA are shifted to red, (ii) the absorbance is slightly decreased whereas emission intensity is increased largely with an increasing β-CD concentration, (iii) BCA forms 1:1 inclusion complex with β-CD and (iv) intramolecular charge transfer (ICT) emission is present in the excited state.