Greatest Wall Street Movies of All Time

Greed is not good. But it sure can be entertaining.

Greatest Wall Street Movies of All Time

Leonardo DiCaprio in The Wolf of Wall Street — Is "The Wolf of Wall Street" Leonardo DiCaprio's best movie?

Greed is not good, but there's something great about taking a complicated topic like stock markets and finance and breaking everything down into a movie the general public can consume and understand.

The films that do this best are endlessly rewatchable. With the uncertain state of the economy and financial markets, now is a good time to invest your time in some movies about money and finance.

These are the greatest Wall Street movies of all time.

30. Cosmopolis

Cosmopolis — This is not a still from Robert Pattinson's next movie, "The Batman."

Year: 2012

Director: David Cronenberg

Starring: Robert Pattinson, Paul Giamatti, Samantha Morton, Sarah Gadon, Mathieu Amalric, Juliette Binoche, Jay Baruchel

Budget: $20.5 million

Worldwide box office: $6.1 million

Rotten Tomatoes audience score: 31%

Streaming: Amazon Prime, Tubi, Pluto TV

Bottom line: There are two really weird, cool Hollywood players in the mix here with director David Cronenberg and leading man Robert Pattinson teaming up to bring a Don DeLillo novel to life.

The movie was a huge box-office bomb, but it's worth watching for Pattinson, who has been steady if not spectacular in leading roles for a decade now, and the audacity of Cronenberg as a director. Don't forget this is the same guy who made "The Fly," "Dead Ringers" and "A History of Violence."

The two of them somehow make watching Pattinson's character's descent from billionaire to dead broke and into murderous madness pretty entertaining.

29. 1929: The Great Crash

1929: The Great Crash — The Great Depression arose after Black Monday on Wall Street in 1929.

Year: 2009

Director: Joanna Bartholomew

Starring: N/A

Budget: N/A (BBC Two documentary)

Worldwide box office: N/A

Rotten Tomatoes audience score: N/A

Streaming: YouTube

Bottom line: One of the great warnings from history is that if we don't understand our past, we're condemned to repeat it. That is in sharp focus with many of the movies on the list, including this British-produced documentary about the stock market crash on Oct. 16, 1929 — Black Tuesday — that led to The Great Depression.

This one should be required viewing for anyone who wants to understand the modern economy because it shows how without regulation of banks, as much as those regulatory agencies are criticized, the alternative is much, much worse.

28. Rogue Trader

Rogue Trader — Ewan McGregor played Nick Leeson, one of the biggest crooks in financial history.

Year: 1999

Director: James Reardon

Starring: Ewan McGregor, Anna Friel, Pip Torrens, Tim McInnerny

Budget: $12.8 million

Worldwide box office: $1.3 million

Rotten Tomatoes audience score: 52%

Streaming: YouTube

Bottom line: This movie took a bath at the box office, but the true story of corrupt derivatives trader Nick Leeson gets a huge boost from the presence of a young Ewan McGregor in one of his last roles before the "Star Wars" prequels turned him into an A-List star for the next decade.

Never heard of Leeson? He single-handedly brought down Barings Bank, which had operated in England since 1762, with a series of fraudulent and unauthorized trades in 1995 that led to $1.4 billion in losses — double what Barings had available.

He fled to Singapore, where he was caught and sentenced to six-and-a-half years in prison. And Singapore prisons are pretty rough.

27. Strictly Business

Strictly Business — Halle Berry was awesome in 1991 and still is in 2021.

Year: 1991

Director: Kevin Hooks

Starring: Tommy Davidson, Joseph C. Phillips, Halle Berry, Kim Coles, Sam Rockwell, Anne-Marie Johnson, David Marshall Grant, Samuel L. Jackson

Budget: $2.5 million

Worldwide box office: $7.6 million

Rotten Tomatoes audience score: 57%

Streaming: Amazon Prime ($)

Bottom line: This movie is largely forgotten aside from being one of Oscar-winning actress Halle Berry's first roles, but it's a pretty lighthearted romp that capitalized on having up-and-coming comedian Tommy Davidson with top billing.

It also featured some lower-level stars who catapulted to fame in later years. Alongside Berry, future Oscar nominees Sam Rockwell and Samuel L. Jackson had supporting roles.

Director Kevin Hooks went on to direct some big-budget action movies in "Passenger 57" and "Fled," and was one of the key directors on the hit TV show "Prison Break."

26. Other People's Money

Other People's Money — Danny DeVito was an A-List Hollywood star in the 1980s and 1990s. Wrap your head around that.

Year: 1991

Director: Norman Jewison

Starring: Danny DeVito, Gregory Peck, Penelope Ann Miller, Piper Laurie

Budget: N/A

Worldwide box office: $25.6 million

Rotten Tomatoes audience score: 46%

Streaming: Hulu, Amazon Prime

Bottom line: You can't help but watch Danny DeVito's starring role in "Other People's Money" and feel like he came so close to hitting the mark with a "Wall Street"-style role.

The problem with "Other People's Money" is that it pulls its punches with its ending. Things that get wrapped up in a tidy manner aren't always what we're looking for from movies.

Sometimes, it's totally OK if not everybody gets their wish. Or if the main character isn't always totally likable.

25. Boom Bust Boom

Boom Bust Boom — These puppets came from the mind of the same guys who made Monty Python.

Year: 2016

Director: Terry Jones, Ben Jones and Ben Timlett

Starring: Terry Jones (narrator), various puppets

Budget: N/A

Worldwide box office: N/A

Rotten Tomatoes audience score: 72%

Streaming: Amazon Prime, Tubi

Bottom line: If you've got the team behind Monty Python making a movie about how we continue to put ourselves in the same situations financially — as countries with the largest GDPs — then you know it's going to have a weird twist.

In this case, that weird twist is making the documentary with a mix of puppets, animation, narration from Monty Python member Terry Jones and interviews with leading economists.

As far as documentaries about financial collapses and society falling apart go, this is probably the funniest.

24. Money for Nothing

John Cusack — John Cusack took a big swing and missed with "Money for Nothing" in 1993.

Year: 1993

Director: Ramon Menendez

Starring: John Cusack, Michael Madsen

Budget: $11 million

Worldwide box office: $1 million

Rotten Tomatoes audience score: 31%

Streaming: Amazon Prime ($)

Bottom line: John Cusack took a shot at a big-fisted drama in the prime of his career, but this movie became known more for its abject failure at the box office and the horrid reviews it received, save for Cusack's performance.

To that end, Cusack is the best part of the movie, which is based on the life story of unemployed Philadelphia longshoreman Joey Coyle, who recovered $1.2 million after it fell out of an armored bank leaving the Federal Reserve.

Eagle-eyed viewers can spot James Gandolfini and future Oscar winners Benicio del Toro and Phillip Seymour Hoffman in supporting roles.

23. Wall Street: Money Never Sleeps

Wall Street: Money Never Sleeps — Michael Douglas stepped back into his role as Gordon Gekko 23 years after the original "Wall Street" came out.

Year: 2010

Director: Oliver Stone

Starring: Michael Douglas, Shia LaBeouf, Josh Brolin, Carey Mulligan, Eli Wallach, Susan Sarandon, Frank Langella

Budget: $70 million

Worldwide box office: $134.7 million

Rotten Tomatoes audience score: 44%

Streaming: Amazon Prime

Bottom line: It's not that this is a bad movie — not by a long shot. It's just that it paled in comparison to its 1987 predecessor, which brought home the Academy Award for Best Actor for Michael Douglas, who reprises his role as Gordon Gekko.

Still, this movie almost doubled its budget at the box office and includes an up-and-coming young star in Shia LaBeouf (essentially in the Charlie Sheen role), who saw his personal life come off the rails shortly after the film's release.

22. The Laundromat

The Laundromat — Netflix thought it was going to strike Oscar gold with "The Laundromat."

Year: 2019

Director: Steven Soderbergh

Starring: Meryl Streep, Gary Oldman, Antonio Banderas, Jeffrey Wright, Robert Patrick, David Schwimmer, Rosalind Chao, Sharon Stone

Budget: N/A (Netflix)

Worldwide box office: N/A

Rotten Tomatoes audience score: 40%

Streaming: Netflix

Bottom line: Netflix takes several big Oscar swings every year and this was one of them in 2019. Even if it was a miss.

Here's the thing though. It's got Meryl Streep. And if you've got Meryl Streep in a movie, there's a chance it's going to be pretty good. The problem here isn't so much with the acting.

It's with the convoluted plot about the Panama Papers — a massive online leak of 11.5 million documents that revealed offshore accounts and investors around the world (many of them involved in illegal deals) and shepherded by Panamanian law firm Mossack Fonseca.

21. Money Monster

Money Monster — "Money Monster" was directed by Oscar winner Jodie Foster and starred Oscar winners Julia Roberts and George Clooney.

Year: 2016

Director: Jodie Foster

Starring: George Clooney, Julia Roberts, Jack O'Connell, Dominic West, Caitriona Balfe, Giancarlo Esposito

Budget: $27.4 million

Worldwide box office: $93.3 million

Rotten Tomatoes audience score: 58%

Streaming: HBO Max, Amazon Prime

Bottom line: George Clooney stars as a Jim Cramer-style host of a TV show, "Money Monster," based on Cramer's real-life show "Mad Money." And if you don't look very deeply at what's going on, it works.

"Money Monster," directed by Jodie Foster, got mixed reviews, but part of that may have been with its drama-heavy marketing. We think it's actually more of a thriller.

And you know what? "Money Monster" made a lot of money, more than tripling its budget at the box office.

20. Barbarians at the Gates

Barbarians at the Gate — James Garner had swag by the boatload.

Year: 1993

Director: Glenn Jordan

Starring: James Garner, Jonathan Pryce, David Rasche, Fred Dalton Thompson, Peter Riegert

Budget: N/A (HBO Films)

Worldwide box office: N/A

Rotten Tomatoes audience score: 75%

Streaming: YouTube

Bottom line: Based on the book by investigative journalists Bryan Burrough and John Helyar about the hostile takeover of RJR Nabisco, "Barbarians at the Gate" was such a big hit in 1993 that after being shown on HBO, it was also shown on FOX.

The reason it was such a big hit was almost solely because of the dynamo presence of the late James Garner.

Garner won the Golden Globe for Best Actor in a Miniseries or Movie and lifted the film to the Primetime Emmy Award for Best Television Movie and Golden Globe for Best Television Movie.

19. The Company Men

The Company Men — "The Company Men" had four Oscar winners in its main cast, including Ben Affleck.

Year: 2010

Director: John Wells

Starring: Ben Affleck, Tommy Lee Jones, Chris Cooper, Kevin Costner, Maria Bello, Rosemarie Dewitt, Craig T. Nelson

Budget: $15 million

Worldwide box office: $8.1 million

Rotten Tomatoes audience score: 55%

Streaming: Hulu, Amazon Prime, Starz

Bottom line: This is a very well-done, little-seen movie that somehow manages to wrangle four Oscar winners onto its cast with Ben Affleck, Tommy Lee Jones, Chris Cooper and Kevin Costner.

The movie's lack of success at the box office can point to bad timing in regard to one cast member. It came out right as Affleck's career renaissance was happening, and if it's delayed maybe six months, it gets much better play.

Director David Wells sparkles in his movie directorial debut. He'd already made a name for himself as the showrunner on hit TV shows like "ER," "The West Wing" and "Shameless."

18. Too Big to Fail

Too Big to Fail — "Too Big to Fail" was one of the last films for famed director Curtis Hanson.

Year: 2011

Director: Curtis Hanson

Starring: William Hurt, Billy Crudup, Paul Giamatti, Topher Grace, Cynthia Nixon, Bill Pullman, Tony Shalhoub, James Woods

Budget: N/A (HBO Films)

Worldwide box office: NA

Rotten Tomatoes audience score: 76%

Streaming: HBO Max, Hulu, Amazon Prime

Bottom line: One of the last films directed by the late Curtis Hanson ("L.A. Confidential," "8 Mile," "Wonder Boys") is a slow burn and was one of the most honored television films of 2011, raking in 11 Primetime Emmy Award nominations. It also scored a Screen Actors Guild Best Actor in a Television Film or Miniseries Role award for Paul Giamatti as Ben Bernanke.

The real star here, however, is William Hurt as U.S. Treasury Secretary and former Goldman Sachs CEO Henry Paulson, a man given the task of making sure the world economy doesn't collapse following the financial housing crisis in 2008.

17. The Secret of My Success

The Secret of my Success — Michael J. Fox could turn a $10 million film into $100 million at the box office.

Year: 1987

Director: Herbert Ross

Starring: Michael J. Fox, Helen Slater, Richard Jordan, Margaret Whitton

Budget: $15 million

Worldwide box office: $111 million

Rotten Tomatoes audience score: 58%

Streaming: HBO Max, Amazon Prime

Bottom line: There are parts of the 1987 box-office smash "The Secret of My Success" that didn't age very well, but it's hard to deny the star power of Michael J. Fox in the mid-to-late 1980s.

How else can we explain the success of this film, that made almost $100 million at the box office? The plot involving Fox as a lowly mailroom delivery person who becomes the head of a Fortune 500 company is almost too stupid to comprehend.

But thanks to Fox, they somehow pull it off.

16. Inside Job

inside Job — One of the "good" guys in "Inside Job" is Eliot Spitzer if that tells you anything.

Year: 2010

Director: Charles Ferguson

Starring: Matt Damon (narrator)

Budget: $2 million

Worldwide box office: $7.9 million

Rotten Tomatoes audience score: 91%

Streaming: YouTube

Bottom line: This Academy Award winner for Best Documentary Feature gives us a look at the big picture when it comes to "worldwide systemic corruption" in our financial systems worldwide.

Narrated by Oscar-winner Matt Damon, the documentary is divided into five parts that trace the U.S. economy through its first period of regulation following the Great Depression, through the catastrophic results of deregulating the banks in the early 1980s and through the housing crisis in the late 2000s.

It's as epic as it sounds.

15. The Wizard of Lies

The Wizard of Lies — Robert DeNiro is scary good playing Bernie Madoff.

Year: 2017

Director: Barry Levinson,

Starring: Robert De Niro, Michelle Pfeiffer, Alessandro Nivola, Hank Azaria, Nathan Darrow, Kristen Connoly, Kathrine Narducci

Budget: N/A (HBO Films)

Worldwide box office: N/A

Rotten Tomatoes audience score: 63%

Streaming: HBO Max

Bottom line: Based on the true story of the largest financial fraud in U.S. history, Robert DeNiro shines as Bernie Madoff, who owned and operated a Wall Street investment firm that scammed a reported $64.8 billion from clients.

The truly heartbreaking stuff in the film comes from Madoff's relationships with his wife, played by Michelle Pfeiffer, and his children.

And nothing is darker than after Madoff is sentenced to 150 years in prison and his family deals with the fallout from his crimes.

14. Boiler Room

Boiler Room — "Boiler Room" is a film that we could put in a time capsule if we want to explain the late 1990s.

Year: 2000

Director: Ben Younger

Starring: Giovanni Ribisi, Vin Diesel, Nia Long, Nicky Katt, Scott Caan, Ben Affleck, Tom Everett Scott

Budget: $7 million

Worldwide box office: $28 million

Rotten Tomatoes audience score: 78%

Streaming: Amazon Prime ($)

Bottom line: If you ever feel like diving into the late 1990s, watch "Boiler Room" and its assembly of an All-Star lineup from that period — including Vin Diesel, Ben Affleck, Scott Caan, Giovanni Ribisi and Nia Long.

This movie works as a financial flick, with a lot of the same stock thieving points as "The Wolf of Wall Street," and also as a thriller.

Over time, the movie has drawn some rightful comparisons to another financial classic, "Glengarry Glen Ross," for its ensemble cast.

13. Die Hard with a Vengeance

Die Hard with a Vengeance — Bruce Willis and Samuel L. Jackson starred in "Pulp Fiction" and "Die Hard with a Vengeance."

Year: 1995

Director: John McTiernan

Starring: Bruce Willis, Samuel L. Jackson, Jeremy Irons, Graham Greene, Colleen Camp, Larry Bryggman, Sam Phillips

Budget: $90 million

Worldwide box office: $366.1 million

Rotten Tomatoes audience score: 83%

Streaming: HBO Max, Amazon Prime, Hulu, Cinemax

Bottom line: What is it about the "Die Hard" movie franchise that makes a clear-cut series of action movies expand across genres? Just like the original has an argument for being a Christmas movie, we can make the case for "Die Hard with a Vengeance" being a Wall Street movie.

Two plot points in particular get DHWAV on the list — the attempted bombing of the Wall Street subway station by villain Jeremy Irons and the main plot point of trying to steal $140 billion in gold bullion from the Federal Reserve.

See how easy that was?

12. Arbitrage

Arbitrage — "Arbitrage" is a thriller disguised as a Wall Street movie.

Year: 2012

Director: Nicholas Jarecki

Starring: Richard Gere, Susan Sarandon, Tim Roth, Brit Marling, Laetitia Casta, Nate Parker

Budget: $12 million

Worldwide box office: $35.5 million

Rotten Tomatoes audience score: 62%

Streaming: Hulu, Amazon Prime, Epix, Sling TV

Bottom line: This movie kind of sums up a lot of Richard Gere's career — underrated and awesome and with him as the leading man.

Gere is cooking with gas in this role as a Bernie Madoff-type broker who runs a Wall Street fund with his daughter, tries to pull off a billion-dollar deal (with half of it in money that doesn't really exist) and then gets caught up in a murder.

There's also some great turns with Susan Sarandon, Tim Roth and Brit Marling in supporting roles, and a twist ending that shows why Gere earned a Golden Globe nomination for Best Actor in a Drama.

11. 99 Homes

99 Homes — Michael Shannon and Andrew Garfield are electric together on the screen.

Year: 2014

Director: Ramin Bahrani

Starring: Andrew Garfield, Michael Shannon, Laura Dern

Budget: $8 million

Worldwide box office (budget): $1.9 million

Rotten Tomatoes audience score: 78%

Streaming: Crackle, Tubi

Bottom line: Two of the better actors to come up in the last two decades, Michael Shannon and Andrew Garfield, get a chance at a two-fisted drama chronicling a corrupt real estate investor and his assistant, who he actually had evicted from his family home.

In a sense, "99 Homes" is really a morality play, and with Shannon and Garfield at the heart, it's really easy to get sucked up into cheering for Garfield no matter what he does because he has such a great screen presence.

Does the ending seem too tidy? Maybe, but we still loved it.

10. The Pursuit of Happyness

The Pursuit of Happyness — If you say you didn't cry at this part of the movie, you're lying.

Year: 2006

Director: Gabriele Muccino

Starring: Will Smith, Jaden Smith, Thandie Newton

Budget: $55 million

Worldwide box office: $307.1 million

Rotten Tomatoes audience score: 87%

Streaming: Philo

Bottom line: Here's how big of a star Will Smith was by 2006. A gutwrenching drama about a homeless San Francisco man struggling to make his way through an internship at a brokerage firm made over $300 million at the box office.

What propels the movie is Smith's charm, charisma and vulnerability, no doubt given a huge lift by having his son, Jaden, play his character's son as they struggle to make it out of poverty.

The movie was based on the true story of stockbroker Chris Gardner, and Smith received his second Academy Award nomination for Best Actor for his role.

9. Glengarry Glen Ross

Glengarry Glen Ross — Always. Be. Closing.

Year: 1992

Director: James Foley

Starring: Al Pacino, Jack Lemmon, Alec Baldwin, Ed Harris, Alan Arkin, Kevin Spacey, Jonathan Pryce

Budget: $12.5 million

Worldwide box office: $10.7 million

Rotten Tomatoes audience score: 88%

Streaming: Hulu, Amazon Prime

Bottom line: Just an absolute classic.

Based on David Mamet's Pulitzer Prize-winning play of the same name, we get Oscar winners and Oscar nominees almost all the way across the board playing a group of real estate salesmen willing to use whatever dubious means they can to save their jobs when they're told by a corporate trainer only two of them will ultimately be retained.

Every performance in "Glengarry Glen Ross" seems like a home run, but ultimately it's Alec Baldwin's berating of the real estate agents and his "Always Be Closing" monologue that still captures our imaginations.

8. American Psycho

American Psycho — This is the look of a man about to do some bad things.

Year: 2000

Director: Mary Harron

Starring: Christian Bale, Chloe Sevigny, Willem Dafoe, Jared Leto, Josh Lucas, Samantha Mathis, Justin Theroux, Reese Witherspoon

Budget: $7 million

Worldwide box office: $34.3 million

Rotten Tomatoes audience score: 85%

Streaming: Peacock

Bottom line: The journey of "American Psycho" from one of the most controversial books of all time to the silver screen wasn't a straight line.

Director Mary Harron and Christian Bale were actually replaced by Oliver Stone and Leonardo DiCaprio during the development process. Then when Stone and DiCaprio backed out, the original director and star were brought back in.

Harron's direction is deft, but Bale absolutely steals the show as serial killer/Wall Street broker Patrick Bateman, and small roles from Chloe Sevigny, Jared Leto, Reese Witherspoon, Justin Theroux and Josh Lucas early in their careers keep the film moving.

7. Enron: The Smartest Guys in the Room

Enron: The Smartest Guys in the Room — If you trusted Jeff Skilling with your money, we're sorry.

Year: 2005

Director: Alex Gibney

Starring: Andrew Fastow, Jeff Skilling, Kenneth Lay, Gray Davis

Budget: $700,000

Worldwide box office: $4.9 million

Rotten Tomatoes audience score: 87%

Streaming: Amazon Prime, Sling TV

Bottom line: Legendary film critic Roger Ebert probably said it best in his review of this Oscar-nominated documentary — "This is not a political documentary. It's a crime story."

He also pointed out that watching the story of one of the biggest business frauds in U.S. history unfold won't just make you think. It will make you mad. Enron and its leaders, Kenneth Lay and Jeff Skilling, were leading a crooked company from the start, and nothing is worse than when they laugh about profiting off the California energy crisis.

Now 16 years after its release, director Alex Gibney is in the running for best documentary filmmaker of all time.

6. Working Girl

Working Girl — "Working Girl" made Melanie Griffith an A-List actress.

Year: 1988

Director: Mike Nichols

Starring: Harrison Ford, Sigourney Weaver, Melanie Griffith, Alec Baldwin, Joan Cusack

Budget: $28.6 million

Worldwide box office: $102 million

Rotten Tomatoes audience score: 67%

Streaming: Showtime, Hulu, Amazon Prime

Bottom line: This movie was a monster box office hit in 1988 thanks to the frowned-upon decision to cast Melanie Griffith in the leading role as young stock trader Tess McGill opposite Harrison Ford and Sigourney Weaver.

It was a star-making role for Griffith, who was nominated for an Academy Award for Best Actress. The film also was nominated for Best Picture, Best Director, Best Supporting Actress for Joan Cusack, and Carly Simon won an Oscar for Best Song for "Let the River Run."

5. Margin Call

Margin Call — "Margin Call" is a vastly underrated film.

Year: 2011

Director: J.C. Chandor

Starring: Paul Bettany, Jeremy Irons, Kevin Spacey, Zachary Quinto, Penn Badgley, Simon Baker, Demi Moore, Stanley Tucci

Budget: $3.5 million

Worldwide box office: $19.5 million

Rotten Tomatoes audience score: 74%

Streaming: Peacock

Bottom line: This movie is interesting because its top-billed stars — Kevin Spacey and Jeremy Irons — chew up plenty of scenery, but it's the younger stars who really deliver the goods, along with too-brief appearances by Demi Moore and Stanley Tucci.

Led by Paul Bettany and Zachary Quinto as the frontline soldiers for an unnamed investment firm, this film moves along at a pace that's not common for Wall Street movies thanks to director J.C. Chandor, who has had a pretty respectable career directing action movies.

4. Wall Street

Wall Street — The two biggest stars in Hollywood, circa 1987.

Year: 1987

Director: Oliver Stone

Starring: Michael Douglas, Charlie Sheen, Martin Sheen, Daryl Hannah, Hal Holbrook, Terence Stamp

Budget: $16.5 million

Worldwide box office: $43.8 million

Rotten Tomatoes audience score: 81%

Streaming: Amazon Prime ($)

Bottom line: When you get your frontline stars all at the peak moments in their careers, or on their way up to that moment, you usually can bottle magic. That's what happens with "Wall Street" with the combination of stars Michael Douglas, Charlie Sheen and writer/director Oliver Stone.

Douglas, playing Gordon Gekko, utters the famous line "Greed is good" and rode it to his only Academy Award for Best Actor win. Sheen beat out Tom Cruise for the role of Douglas' protege.

Oliver Stone's five-year stretch rivals any director in cinematic history — "Platoon" (1986), "Wall Street" (1987), "Born on the Fourth of July" (1989), "The Doors" (1991) and "JFK" (1991).

3. The Big Short

The Big Short — "The Big Short" had a lot of bad haircuts.

Year: 2015

Director: Adam McKay

Starring: Christian Bale, Brad Pitt, Steve Carrell, Ryan Gosling, John Magaro, Finn Wittrock, Jeremy Strong, Marisa Tomei

Budget: $50 million

Worldwide box office: $133.4 million

Rotten Tomatoes audience score: 88%

Streaming: Crackle

Bottom line: The big bets in Hollywood were against director Adam McKay being able to pull off a movie about a complicated financial story. The thought was the director of hits like "Anchorman" and "Step Brothers" wouldn't be able to pull off the right tone.

Man, were they ever wrong. McKay's opus about the 2008 housing collapse was a box-office hit and a ratings darling, bringing in five Academy Awards nominations — including Best Picture.

McKay was nominated for Best Director and won the Oscar for Best Adapted Screenplay.

2. Trading Places

Trading Places — Looking good, Billy Ray! Feeling good, Louis!

Year: 1983

Director: John Landis

Starring: Eddie Murphy, Dan Aykroyd, Ralph Bellamy, Don Ameche, Denholm Elliott, Jamie Lee Curtis

Budget: $15 million

Worldwide box office: $90.4 million

Rotten Tomatoes audience score: 85%

Streaming: Hulu, Starz

Bottom line: Not every part of "Trading Places" aged very well, but the sheer star power of Eddie Murphy, Dan Aykroyd and Jamie Lee Curtis early in their careers propels this movie into the stratosphere.

It is one of those movies that you just can't watch or rewatch without doubling over in laughter and the mega box-office numbers — an adjusted take of $240.1 million in today's money — speaks to what a hit this was for all involved.

Director John Landis reteamed with Murphy for "Coming to America" — one of the greatest comedies of all time.

1. The Wolf of Wall Street

The Wolf of Wall Street — Is this the greatest screen duo in history? We like to think so.

Year: 2013

Director: Martin Scorses

Starring: Leonardo DiCaprio, Jonah Hill, Margot Robbie, Kyle Chandler, Matthew McConaughey, Rob Reiner, Jon Favreau, Jean Dujardin, Jon Bernthal

Budget: $100 million

Worldwide box office: $392 million

Rotten Tomatoes audience score: 83%

Streaming: Amazon Prime ($)

Bottom line: There is no more clear-cut No. 1 movie about money, finances or Wall Street than Leonardo DiCaprio's rocket-launcher performance as "The Wolf of Wall Street" Jordan Belfort.

This movie is infinitely rewatchable, and the 1-2 punch of DiCaprio alongside Jonah Hill rivals the very best screen duos of all time.

Nominated for five Academy Awards, the story of how this movie was made thanks to corrupt Malaysian financier Jho Low is almost as wild as the story itself.