Each smile is unique: one person surely smiles in different ways (e.g. closing/opening the eyes or mouth). Given one input image of a neutral face, can we generate multiple smile videos with distinctive characteristics? To tackle this one-to-many video generation problem, we propose a novel deep learning architecture named Conditional Multi-Mode Network (CMM-Net). To better encode the dynamics offacial expressions, CMM-Net explicitly exploits facial landmarks for generating smile sequences. Specifically, a variational auto-encoder is used to learn a facial landmark embedding. This single embedding is then exploited by a conditional recurrent network which generates a landmark embedding sequence conditioned on a specific expression (e.g. spontaneous smile). Next, the generated landmark embeddings are fed into a multi-mode recurrent landmark generator, producing a set of landmark sequences still associated to the given smile class but clearly distinct from each other Finally, these landmark sequences are translated into face videos. Our experimental results demonstrate the effectiveness of our CMM-Net in generating realistic videos of multiple smile expressions.