The album includes lively renditions of standards such as "When You're Smiling," "Blue Moon," and "S'posin'." It captures the essence of Sinatra's ability to bring a fresh and dynamic interpretation to well-known songs. The production is marked by its crisp, upbeat tempo, and the seamless interplay between Sinatra's vocals and the big band instrumentation. "Sinatra's Swingin' Session!!!" stands as a testament to Sinatra's enduring appeal and his masterful collaboration with Nelson Riddle, delivering a vibrant addition to his extensive catalog of swing music.