As an important carrier of Chinese culture, Chinese calligraphy has unique value in transnational cultural communication.In this research paper, we develop a Chinese character calligraphy generation system to implement the application of Chinese character calligraphy style transfer technology in cross – national cultural communication. After conducting in – depth research on style transfer technology and CycleGAN, we build a Chinese character calligraphy generation model named CRA – GAN. This model is aimed at enhancing the quality of generated Chinese character calligraphy. Subsequently, a Chinese character calligraphy generation system is designed to boost the cross – national cultural dissemination of Chinese character calligraphy. The CRA – GAN model designed in this paper shows excellent performance in the task of converting the style of Chinese character calligraphy, and the model has high values of SSIM, FSIM, PSNR and low values of RMSE, and the mean value of subjective evaluation of the generated Chinese characters by professionals is mostly 8 or 9 points. It was verified by linear regression that after the application of the Chinese character calligraphy generation system, the attitudes of expatriates towards Chinese character culture were significantly improved, and the realization of the Chinese character calligraphy style migration technology is of great significance for transnational cultural communication.