WingMan follows the journey of Mitch Wolfe, a former Hollywood executive who has now hit rock bottom. He is considered a laughingstock in the film industry due to his inability to produce a successful movie in recent years, which has caused him financial ruin and a trail of debt. In a desperate attempt to revive his career, Mitch makes the decision to flee to Cuba in the hopes of receiving funding to produce his last movie.
Things do not go as planned for Mitch in Cuba as he discovers that the local film industry is far removed from Hollywood's glamour and glitz. Instead, he is faced with challenges such as language barriers, cultural differences, and some corrupt officials. To make matters worse, Mitch is approached by his former associates who he suspects are after him to collect on his debt.
Amidst his struggles, Mitch meets a local nurse, Ana, who becomes his guide and helps him connect with the local filmmakers who eventually agree to help him produce his movie. However, when the crew discovers the meddlesome and delusional style of Mitch's directing, their patience and efforts are put to the test, causing a rift between them.
As the production progresses and Mitch's erratic behavior intensifies, he is forced to confront the harsh realities of his situation. Will Mitch be able to direct the perfect film and resurrect his career, or will his delusions and personality ultimately lead to his downfall?