Higher and Higher

Cyrus Drake's bankruptcy is revealed and a foreclosure looms over the estate. The household staff hasn't been paid for seven months, adding to the tension. With the wife and daughter abroad on a long trip, the Drakes have little cushion to weather the crisis.

To save the family fortune, a scheme is hatched to pass Millie off as Pamela Drake, the Drakes' socialite daughter, and marry her to a wealthy man. The aim is to bring in funds to cover the mounting debts and keep the business afloat.

Valet Mike O'Brien is enlisted to help Millie prepare for life as a debutante, coaching her through diction and manner. He remains unaware that Millie secretly loves him, keeping his own feelings in check amid the scheme.

Millie mentions she adores the neighbor who sings, a nod to Frank Sinatra whose crooning delights the bobby-sockers. The dialogue and jokes lightly poke fun at pop stars of the era while Millie finds inspiration in the music.

The social secretary Sandy begins teaching Millie proper etiquette, guiding her to walk, speak, and behave like a debutante. The training is meant to polish her image for high society.

At the coming-out ball, Millie is nudged toward Sir Victor Fitzroy Victor, a titled nobleman she should marry. Georgia Keating, a high-society friend, pushes for Millie to be considered the most desirable debutante.

Victor cannot even pay his hotel bill and is actually a petty thief named Joe Brown. He intends to trap a rich wife to cover his own debts.

Despite doubts, Millie agrees to marry Victor for the sake of her family and the Drakes' finances. The plan hinges on securing the Drakes' finances through the marriage.

Mike mistakenly believes Millie is in love with Frank and helps her get out of the wedding at the last minute. He acts to protect her and the truth of her feelings.

Mike stumbles upon a hidden speakeasy in the Drake basement, discovering the Drake family's valuable first harpsichord and a fully stocked wine cellar. The secret space hints at a potential new revenue source.

The basement space opens as Drake's Amsterdam Tavern, New York's most novel nightclub, transforming the way the Drakes can earn money. The venture begins to solve the financial crisis.

Victor, now going by Joe Brown, works behind the bar at the new club, maintaining his disguise while the family’s fortunes rise.

Realizing Millie can only be happy with Frank, Mike bows out so she can be with the singer. He leaves to resume his vaudeville career, choosing love over the stage.

Mike receives an invitation to Frank and Katherine's wedding and uses it as a trigger to confront Frank for spurning Millie. He wants a clear sense of where Millie's heart truly lies.

At the finale, Mike learns that Millie has only ever loved him. They share a romantic dance and begin their romance, dancing Higher and Higher into the clouds as their feelings are finally acknowledged.