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

September 24, 2025/ 47 min/ Sean Fennessey · Amanda Dobbins

The 25-for-25 countdown reaches No. 11, and Sean Fennessey and Amanda Dobbins spend it on the Scorsese entry: 'The Wolf of Wall Street,' the movie they both think they ranked too low. They get into the DiCaprio-financed $100 million shoot, the 180-minute excess and whether it endorses what it shows, the 30-plus needle drops, and where the Jordan Belfort performance lands in DiCaprio's career.

1 films across 1 segment.

AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.

No. 11 on the countdowna 25-for-25 special conversation

The Wolf of Wall Street poster

The Wolf of Wall Street 2013

Sean and Amanda's unanimous Scorsese pick, and the one they keep saying is too low at No. 11. Written by Terence Winter from Jordan Belfort's memoir, shot by Rodrigo Prieto, with Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McConaughey, Kyle Chandler, Rob Reiner, Jon Bernthal, and Jon Favreau. DiCaprio raised about $100 million to make it independently, since no studio would greenlight the opening, and it became Scorsese's biggest hit at roughly $400 million worldwide. They read the 180-minute bacchanal as the point rather than an endorsement, and flag the 30-plus needle drops and the slowed-down blues that scores Belfort's descent. They also tie the film to Trump-era New York excess and argue this is DiCaprio's best performance of the century.

Also mentioned raised along the way

Scorsese's eligible century Gangs of New YorkThe AviatorThe DepartedShutter IslandHugoSilenceThe IrishmanKillers of the Flower Moon

The best-DiCaprio-performance debate Django UnchainedJ. EdgarThe RevenantOnce Upon a Time in HollywoodCatch Me If You CanDon't Look UpOne Battle After AnotherBody of LiesRevolutionary RoadTitanicRomeo + JulietThis Boy's Life

If you like it Boiler RoomMargin CallWall StreetThe Big Short

In passing GoodfellasTaxi DriverMegalopolisFrankensteinSinners

Not films filtered out: TV, games, ads

TV Mr. ScorseseIndustryLifestyles of the Rich and Famous

Podcasts The Rewatchables

Sports T-Mobile Home Run Derby

Ads State FarmBoar's HeadNetflixStarbucks FrappuccinoStitch Fix