Harold (The Boy) leaves his small hometown of Great Bend for the big city, promising his girlfriend Mildred (The Girl) that he will send for her once he has "made good." In reality, he struggles as a lowly fabric clerk at the De Vore Department Store, surviving on pennies while sending Mildred expensive gifts he cannot afford to maintain the illusion of wealth and success.
When Mildred makes a surprise visit, Harold is forced to impersonate the store's General Manager to keep up his charade. Desperate for money to marry her and cover his lies, he overhears the real manager offering $1,000 to anyone who can attract a massive crowd to the store. Harold pitches a publicity stunt involving his friend, "Limpy" Bill, a steeplejack who will climb the building's exterior.
On the day of the climb, Bill is chased by a policeman he had previously pranked, forcing Harold to take his place. The film culminates in a harrowing comedic ascent where Harold scales the twelve-story skyscraper, facing increasingly dangerous obstacles—including pigeons, a mouse, a net, and a swinging window—while trying to survive the climb and win the prize.
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