Biophysical properties of cellular membranes critically depend on their content of cholesterol and its interaction with various other lipid species. Cholesterol-dependent friction at the nanoscale can be studied with molecular rotors, whose quantum yield depends on rotational dynamics of functional groups during their excited state lifetime. Here, we present a detailed computational analysis of a phenyl-BODIPY-linked cholesterol based molecular rotor in direct comparison with the well-known TopFluor-cholesterol. We describe a new parametrization strategy of force field parameters for the BODIPY moiety and carry out extensive molecular dynamics simulations of the probe in membranes in the absence or presence of cholesterol. Our study quantifies the extent of membrane perturbation by these probes, analyzes their tilting resistance in the bilayer and derives dynamic properties directly related to the rotor propensity. We show that phenyl-BODIPY-cholesterol bears potential as a cholesterol-dependent molecular rotor to report about microviscosity of sterol-containing model and cell membranes.