"Sweet and Lowdown," directed by Woody Allen, is a fictional story and not directly based on a true story. The film follows the life of a fictional jazz guitarist named Emmet Ray, played by Sean Penn, who idolizes Django Reinhardt. While the character and plot are imaginative, they incorporate elements of real jazz history and culture. The film blends fact and fiction, showcasing the jazz scene of the 1930s and highlighting the struggles and triumphs of musicians during that era.

Yes, Sean Penn played guitar in "Sweet and Lowdown." In the film, he portrays Emmet Ray, a talented yet troubled jazz guitarist. To prepare for the role, Penn took guitar lessons to convincingly depict a musician. While his playing was complemented by the music of renowned jazz guitarist Django Reinhardt, Penn's performance included his own guitar work, showcasing his dedication to the character and the art of jazz music. The film, directed by Woody Allen, was released in 1999 and received critical acclaim.