Generative Adversarial Networks (GANs) have shown im-pressive results for image generation. However, GANs facechallenges in generating contents with certain types of con-straints, such as game levels. Specifically, it is difficult togenerate levels that have aesthetic appeal and are playable atthe same time. Additionally, because training data usually islimited, it is challenging to generate unique levels with cur-rent GANs. In this paper, we propose a new GAN architec-ture namedConditional Embedding Self-Attention Genera-tive Adversarial Network(CESAGAN) and a new bootstrap-ping training procedure. The CESAGAN is a modification ofthe self-attention GAN that incorporates an embedding fea-ture vector input to condition the training of the discriminatorand generator. This allows the network to model non-localdependency between game objects, and to count objects. Ad-ditionally, to reduce the number of levels necessary to trainthe GAN, we propose a bootstrapping mechanism in whichplayable generated levels are added to the training set. Theresults demonstrate that the new approach does not only gen-erate a larger number of levels that are playable but also gen-erates fewer duplicate levels compared to a standard GAN.