Wright's elaborate plan to get the money back from Corcoran, the swindler who cheated Susan's mother, is set into action. "Kale," "mazuma," "moola," "lettuce," and "hay" are some of the slang words for money that the characters use in this segment.

Accompanied by an orchestra conducted by Van Dyke Parks, Gaby Moreno and Jackson Browne sing “Across the Borderline," a song first recorded for the 1982 neo-noir film The Border, starring Jack Nicholson.

Dorcas feigns a fainting spell and lures Stan into her hotel room. She suggests they have a Sazerac, a New Orleans cocktail made with either rye whiskey or cognac, together with water, sugar, bitters and absinthe.

Mary Lou and Oliver dance about the hotel room and are interrupted by her husband.

Oliver pretends that he's the Sheriff from Midvale County when he confronts Mary Lou's husband about the swindling of Mrs. Audrey Cowan. From under the chaise lounge, Stan saves the day.

Susan rehearses at the riverboat nightclub, singing “I've Gotta See for Myself” about “the will-o-the-wisp they call love.” A will-o-the wisp is something that is ghost-like and elusive. Vivian Blaine, who plays Susan Cowan, went on to star in the debut of Guys and Dolls on Broadway.

Stan loses at poker and is asked to play a role that he has misgivings about. However, with some coaching from Oliver, Stan admirably rises to the occasion.

Susan sings “The Moon Kissed the Mississippi” to Miss Emily, her supposedly rich aunt and potential investor in Mr. Bennett's show. The song was composed for the film by Lew Pollack and the lyrics are by Charles Newman.

Isaac Slade, singer of the American alternative rock group The Fray, wrote this song about his experiences working as a mentor at a camp for troubled teenagers. Sometimes we just haven’t got the experience and the knowledge to know how to help someone who is going through difficulties.

Miss Emily, who is Stan in disguise, is delighted with Susan and the show. Mr. Bennett thinks he's got Miss Emily on the hook for five thousand dollars. Meanwhile, "Watty" literally empties Mr. Bennett's pockets.

Mr. Bennett wants Tony Queen to advance him five thousand dollars to stuff in an envelope — part of a con to cheat Miss Emily out of her investment in the show. Chester has cooked up a similar swindle involving the switching of envelopes for Stan and Ollie to carry out on Mr. Bennett.

It's time for the envelope routine and both groups are sure they've pulled a fast one. Miss Emily proposes a drink to celebrate while Chester takes the envelope to the hotel safe.

When ​Bennett open​s​ the envelope​,​ Stan and Ollie make a hasty getaway — but not fast enough. Tony Queen plans on turning the showboat into a ​casino, which will include ​roulette and ​the bird cage (a game played with three dice)​. Queen also has plans for Susan.

Ollie is tasked with shoveling coal into the boiler to heat the riverboat while Miss Emmie (Stan) gets to sit it out. Susan entertains the nightclub patrons with a musical number.

The pills meant to turn water into gasoline were a bust, but they come in handy for Stan, Ollie, and Susan. Some of their problems just float away.