My film choice is The Wolf of Wall Street (2013), starring Leonardo DiCaprio as Jordan Belfort who, in 1987, aged 25 years, becomes a Wall Street stockbroker and succumbs to the culture of excess of the time. After losing his job because of Black Monday, he revives his fortunes through fraud and corruption which lead to his eventual downfall.
The screenplay is based on Belfort's 2007 memoir of the same name.
I started work in The City (London's financial district) in 1987, too, and remember vividly the "conspicuous consumption" by some of those around me and their maniacal zeal for more. This film captures the mood well. Thankful I was not a willing participant and remained unscathed.