The Jackie Mason Musical, begins at a deli in Miami in 1977, where Jackie - a renown 46 year old Comedian, spots college girl Ginger - (played by Jackie and the playwright's real life daughter - Sheba Mason - in the OffBroadway production). Along for the ride is her overbearing mom, Mrs. Olivier, and a hilarious cast of five more off-beat characters. Soon Jackie is wooing Ginger each winter whenever he’s in South Florida churning up laughs with the South Beach set. The trouble is, Jackie is also wooing Trixie - a ravishing young Latina Rascal House server, and Rosa - a senior Rascal House server with attitude.
Jackie is a "player", albeit a Delicatessen player, manipulating dates, and times, all managed by a sidekick named Wooley the Shlepalong who is constantly on the go with excuses and fallback plans for the Comic’s escapades - sometimes juggling as many as four women a day - a fact that sends Ginger into romantic distress.
One night Jackie is knocked out by a former fan whom he had previously insulted in a different show several years before. As a result of that insult, the fan (Nelson Zee) lost his job, and his wife.
In the tenth year of their romance, Ginger becomes pregnant, Jackie denies his paternity just as Broadway and stardom emerges and although he is still yearning to be with Ginger, he can’t, and a complicated relationship begins, including Sheba’s own love for the man she knows is her father and whom she wishes she knew. The original score includes “Ode to the Early Bird Special” and “I Never Met This Yenta” and 'The Finger".