We consider adhesion due to London–van der Waals attraction between a thin film and a patterned surface with nanometer asperities. Depending on the surface topography and the stiffness of the film, three regimes of adhesion are identified: complete contact adhesion, partial contact adhesion, and glassy adhesion. For complete contact adhesion, the film conforms to the undulations of the surface, whereas for partial contact and glassy adhesion, the adhesive interface breaks down into microscopic areas of contact. When a film in the glassy regime is peeled off the surface, metastable states develop at which the crack front becomes arrested, analogously to the frustrated motion of the three-phase contact line across a heterogeneous surface. For this glassy regime, we use transition state theory to model the thermally-activated progression of the crack front. This theoretical treatment suggests that the rate of the adhesive failure increases exponentially with the applied force.