Movies Like Wolf of Wall Street That Blend Real and Reel

Back in 2013, Martin Scorcese and Leonardo DiCaprio took audiences on a wild ride with a film unlike any other. And if you’re not quite down from that high, we’ve got a few more movies like Wolf of Wall Street to keep you entertained!

The Wolf of Wall Street is a 2013 biographical black comedy depicting the rise and fall of American entrepreneur, former stockbroker, and convicted felon, Jordan Belfort. The film was based on Belfort’s own memoir of the same name.

When you take the magnitude of talent this film boasts and that its story comes straight from the horse’s mouth, it’s not difficult to see why it was such a huge hit. A comedically dark take on the perils of excess, the pitfalls of the great “American dream,” and ultimately, the depravity of chasing the almighty dollar, Wolf of Wall Street is as much a wild ride as it is a cautionary tale.

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Movies to Watch if You Liked Wolf of Wall Street

Finding movies like Wolf of Wall Street isn’t a difficult task. Many a film has tackled the dangers of greed, and quite a few have done so with a touch of humor. But – and this is one of the criticisms raised against Wolf of Wall Street as well – not many movies can tackle such heavy concepts without somehow also glorying the very thing they critique.

Here are a few more films that depicted the rise and fall of an everyman trying to rub shoulders with elites and meeting his inevitable doom.

War Dogs (2016)

War Dogs is a dark comedy that is loosely based on the real-life story of arms dealers Efraim Diveroli and David Packouz. Specifically, the movie focuses on the duo’s $300 million deal with the U.S. Army to supply ammunition for the Afghan National Army during the Iraq War.

Despite having real events and first-hand accounts to draw from, the film makes several changes and additions to the original story. Yet, it doesn’t shy away from showcasing the depravity of its lead characters, namely Diveroli, Packouz, and the U.S. Army.

The duo vehemently opposes the war, but the allure of millions is too grand for them to care. After all, they have bills to pay and families to feed. And so begins their quest to find ways to meet the demands of their client, despite it putting them in the company of dangerous persons.

Ultimately, War Dogs is a film on the opposite end of the spectrum. Where Wold of Wall Street is about excess, War Dogs is about dearth and living life on survival mode.

American Made (2017)

Tom Cruise tells the real-life story of Barry Seal in American Made. A TWA pilot who flew missions for the CIA, a drug smuggler for the Medellín Cartel, and an informant for the DEA, Seal evidently feared nothing and no one, not even the Devil himself.

Either that or the movie took a lot of creative liberties, including flat-out lying about certain elements that Seal himself swore were untrue when he testified in court. Director Doug Liman himself described the film as nothing more than “a fun lie based on a true story.” Make of that what you will.

Outside of the veracity of its claims, however, American Made does make a good show of what happens when the two sides of the law meet somewhere in the middle: regular people get hurt. Everyday folk get caught up in schemes. Some die. Some get murdered.

And rarely is anyone held accountable for any of it.

Catch Me If You Can (2002)

Catch Me If You Can stars DiCaprio alongside an all-star cast, with Steven Spielberg at the helm. Based on the American conman Frank Abagnale, the film’s accuracy has been called into question by many. Yet, in this case, it isn’t owing to creative liberties. Abagnale’s aggrandizing of his escapades tends to blur the line between fiction and reality, just a touch.

The gist of it all is simple enough: Abagnale conned his way into millionaire status by posing as a pilot, a doctor, and a prosecutor, all before the age of nineteen. His most notable con was as a Pan American pilot. The film’s other plot points touch on broken families, the chasing of a grand dream, and the cat-and-mouse act that Abagnale performs with the FBI on his tail. The same FBI with whom he later cooperates, becoming one of their top experts on fraud and forgery.

That is if you believe anything Abagnale has to say about it. Turns out, when you pick his tale apart, some things don’t add up. Then again, just because it may not have happened is no reason to bore your audience with a dull story.

And Catch Me If You Can is anything but dull.

Goodfellas (1990)

Goodfellas is an adaptation of the book Wiseguy by Nicholas Pileggi. It recounts the story of American mobster Henry Hill and his merry band of associates, spanning several decades of crime and betrayal.

As with several other films on the list, Hill began on one side of crime and transitioned to the other to save himself from an extended prison sentence. As an informant for the FBI, Hill helped bring about fifty convictions. Talk about burning bridges!

Unlike the other films on here, however, Goodfellas is, as Hill himself described it, about 95 percent true. And while it tones down some aspects of reality, the film has the approval of everyone, from critics and audiences to real-life mobsters.

Movies Like Goodfellas and Wolf of Wall Street

Goodfellas is often considered the second greatest gangster film of all time, following the 1972 film, Godfather. It’s easy to see why. Both Goodfellas and Wolf of Wall Street excel in using the talent they’ve gathered to the fullest. When paired with solid direction and a well-written script, it’s impossible to go wrong.

In addition, both films offer well-paced stories that never leave you bored or losing interest, and they give you intriguing and flawed characters who make you question your own long-held beliefs.

Here are a few more movies that manage to accomplish similar feats.

Uncut Gems (2019)

Arguably the best film in Adam Sandler’s career, Uncut Gems is a crime thriller that sees a gambling addict attempting to secure a jewel to clear his debts.

Sandler is more widely known for his less-than-savory comedies. Yet, when given the chance, the actor has proven himself to be an incredibly gifted dramatic actor. In Uncut Gems, Sandler delivers a performance that is both riveting and tragic. Each time he makes a choice, you find yourself compelled to yell at him for his foolishness all while still rooting for him and hoping he makes it out alive.

Much like Wolf of Wall Street, Uncut Gem gives you an intensely flawed lead and allows you to decide whether you want him to succeed or be swallowed whole by his own greed.

American Gangster (2007)

American Gangster is a biographical film based on the life of Harlem trafficker Frank Lucas. The story revolves around Lucas’ business of securing heroin directly from Thailand and smuggling it into U.S. territory via coffins of servicemen returning from the Vietnam War.

Despite being categorized as biographical, all of the individuals involved in the real-life events depicted have confirmed that the film is highly dramatized and contains very little accuracy. Nonetheless, it offers an extremely enjoyable ride and is worth watching for the performances of its leads alone.

And if that isn’t enough, it’s also a pretty good addition to the gangster film genre.

Business Movies Like Wolf of Wall Street

The setting of Wolf of Wall Street is, of course, the stock market. And even if you’re not in the business of finance, the movie does a pretty good job of drawing you into this world.

Here are a few more films built around the finance industry.

The Big Short (2015)

The Big Short is a biographical dramedy based on the financial crisis of 2007-2008. Specifically, it details the events that led to and cause the 2007 housing market crash.

With an all-star cast and the insight contained in American financial journalist Michael Lewis’ book The Big Short: Inside the Doomsday Machine, this movie offers plenty to love, even for those not well-versed with the ins and outs of the economic world.

But the most important takeaway from The Big Short isn’t its talent or its pizzazz. It’s the fact that it is almost entirely true. Predatory behaviors from financial professionals caused a global crash – the worst since The Great Depression – that they refused to take full accountability for.

And as one might guess, it was the little people that suffered the full force of the fallout.

Wall Street (1987)

Wall Street is a drama loosely based on real-life stockbrokers and investors during the Great Depression. While not being a true story itself, Wall Street exemplifies the financial atmosphere of the ‘80s, pitting hard work against unchecked ambition and ultimately depicting the folly of both.

The film begins, as with many others on this list, with an everyman trying to find his big break. He doggedly pursues his icon, doing everything he can to secure his business. When he finally does, the duo takes one another to new professional heights. Yet, when our everyman realizes he has aided a monster, he vows to take him down.

Oddly enough, despite the film being a cautionary tale on the pitfalls of greed, Gordon Gekko’s manipulative villainy would end up being manifested into our living reality with many a stockbroker citing him as their inspiration for entering the field.

Inspirational Movies Like Wolf of Wall Street

Wolf of Wall Street isn’t technically inspiring. Yet, as Wall Street proves, movies like Wolf of Wall Street seem to have the power to move and shape people.

Here are a few films that accomplish something similar while giving us slightly better role models to look up to.

American Hustle (2013)

Inspired by the FBI’s Abscam operation from the ‘70s and ‘80s, American Hustle features an ensemble cast, some flashy direction, and some top-tier dialogue.

The story revolves around two con artists who are coerced into helping the FBI run a sting operation to catch corrupt politicians in the act, so to speak. While the film does take creative liberties, and to that end shouldn’t be treated as a biographical work, it does showcase how corruption can often run rampant and unchecked.

Unlike Wolf of Wall Street and movies like it, however, American Hustle gives its everyman a seemingly happy ending, with the “real” villains left to face the music.

The Pursuit of Happyness (2006)

The Pursuit of Happyness is a biographical drama starring Will Smith as American businessman Chris Gardener.

Gardner began his journey as a salesman struggling to make ends meet. A chance meeting lands him a gig as an unpaid intern stockbroker. Despite barely having money to pay for the ride to work let alone support himself and his son as they battle homelessness, Gardner never gives up, fighting his way out of his situation.

His gumption pays off and hearing the laughter as he and his son walk toward their new future is one of the most heart-warming payoffs a film has ever delivered.

“Greed, for lack of a better word, is good.”

Famous words, uttered by Michael Douglas’ Gordon Gekko in Wall Street. After all, as he argues, greed is simply an evolutionary drive. It’s what pushes us to striver for more. For better. Yet, the unchecked ambition of man is rarely thought to be a virtue. “Too much greed” is considered to be what brings one’s downfall. Desire is a tool of evil. Chase, instead, the reward of hard work and persistence.

Regardless of which side of the line you adhere to – evolutionary greed or ceaseless hard work – there will always be a conman or a stockbroker somewhere making a quick buck off some poor unfortunate soul who has no idea what they just bought into. Leaving in their wake several victims, financial crises, and a darn fine story to sell as the next big film.

Enjoyed this list? Check out Best Thought Provoking Movies of 2021.