Worn by: Josh Brolin as Bretton James
Reference: Vacheron Constantin American 1921
Brand: Vacheron Constantin
In Wall Street: Money Never Sleeps, the sequel to the 1987 financial suspense film, Josh Brolin plays Bretton James, an investment banker who is willing to do anything dirty to make a profit. He wears a Vacheron Constantin Historiques American 1921. The 1920s was the era when Ford started mass-producing automobiles and everyone could enjoy driving their own cars. This reproduction model of a driver's watch, made for car enthusiasts of the time, was chosen to represent the rise and fall of the automobile industry, a symbol of the history of the American economy. It was only natural that this model would appear in this film, which depicts the contrast between the old and new eras of Wall Street.
Source: https://commit-watch.co.jp/en/blogs/column/culture-108
Worn by: Shia LaBeouf as Jacob Moore
Reference: IWC Portugieser
Brand: IWC
The refined and classic design of the IWC Portuguese perfectly complements his role as a young, ambitious Wall Street trader in this sequel to the iconic Wall Street.

Source: https://therake.com/us/stories/the-impact-of-watches-in-cinema