The Big Picture

The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’

September 24, 2025

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  • 'The Wolf of Wall Street' is considered Martin Scorsese's late-career masterpiece and the most conventionally entertaining film from his 21st-century output, despite its controversial subject matter. 
  • Leonardo DiCaprio's performance as Jordan Belfort in 'The Wolf of Wall Street' is argued to be the greatest of his career, showcasing a remarkable range of comedic, dramatic, and physical acting. 
  • The film's excessive portrayal of wealth and debauchery is seen as a deliberate artistic choice by Scorsese to critique the rot at the heart of the American soul and the corrupting influence of money, rather than to glorify it. 

Segments

Scorsese’s 21st Century Filmography
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(00:01:43)
  • Key Takeaway: Martin Scorsese’s 21st-century filmography is characterized by a series of ambitious, durational films exploring obsessions with filmmaking, faith, masculinity, and the American psyche.
  • Summary: Scorsese’s recent work, including ‘Shutter Island,’ ‘Hugo,’ ‘The Wolf of Wall Street,’ ‘Silence,’ ‘The Irishman,’ and ‘Killers of the Flower Moon,’ represents a distinct era of large-scale filmmaking. These films delve into recurring themes such as obsession, faith, masculinity, addiction, and the darker aspects of the American experience.
The Wolf of Wall Street’s Excess and Message
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(00:06:50)
  • Key Takeaway: The excessive and often grotesque portrayal of vice in ‘The Wolf of Wall Street’ serves as a deliberate critique of wealth’s corrupting influence, rather than a glorification of the behavior depicted.
  • Summary: While ‘The Wolf of Wall Street’ is undeniably entertaining and features a high volume of explicit content, this excess is central to its message about the destructive nature of unchecked greed. The film’s script intentionally highlights the depravity of its characters, aiming to gross out the audience and underscore the unsustainable toll of their actions.
DiCaprio’s Performance Evolution
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(00:25:50)
  • Key Takeaway: Leonardo DiCaprio’s performance in ‘The Wolf of Wall Street’ is a career-defining role, showcasing his ability to embody complex, morally ambiguous characters with both charisma and profound vulnerability.
  • Summary: DiCaprio’s portrayal of Jordan Belfort in ‘The Wolf of Wall Street’ is considered his finest, demonstrating a masterful balance of conman bravado, comedic timing, and underlying human frailty. This performance is part of a broader evolution in his career, marked by a willingness to tackle challenging roles in films like ‘Django Unchained’ and ‘Once Upon a Time in Hollywood,’ moving beyond his earlier, more conventional leading man roles.
Thematic Resonance and Cultural Impact
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(00:36:37)
  • Key Takeaway: ‘The Wolf of Wall Street’ functions as a sharp, contemporary critique of American finance and culture, presaging later scandals and reflecting the era’s obsession with wealth and success.
  • Summary: Released in the wake of the 2008 financial crisis, ‘The Wolf of Wall Street’ serves as a potent commentary on the excesses and moral compromises within American finance. The film’s themes of ambition, corruption, and the pursuit of wealth resonate with cultural touchstones like ‘Lifestyles of the Rich and Famous’ and even presage later events, highlighting the enduring allure and danger of the ‘finance bro’ archetype.