After a terrible night of work, a dejected and struggling bartender named Charley stumbles upon a man claiming to be Mark Twain in the alley of the bar where she works. After being sent on his way, Twain manages to befriend a high-school student named Anson in the park by taking the fall for some weed. As a thanks Anson gets his aunt to bail Twain out of trouble. Coincidentally they recognize each other from earlier in the alley. Charley gives Twain a place to stay for helping Anson. The two clash about cultural etiquette in modern Chicago, with Charley revealing that she has a viral scandal ruining her ability to properly pay rent, maintain a relationship with her nephew Anson, or pursue her dreams of stand-up comedy. Twain's unabashed character and tenacity in the face of failure prove to Charley that public opinion has nothing to do with her talent. With newfound confidence Charley is able to return to comedy and heal her relationship with Anson.