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10 Mind Bending Movies Like 21 (That Draw You In)

Updated on August 3, 2019
Harry Sheen profile image

A film buff who enjoys watching a range of different films from funny rom coms to intense thrillers.

21 | Source

It’s a movie that follows a true story. Following on the story of the MIT Blackjack Team, as told by the Ben Mezrich book, Bringing Down the House. It’s a classic story, and one that many people enjoyed at the time. Indeed, when it was released, it was the #1 film in the USA and Canada for two weeks!

It came out over a decade ago now, though, and the chances are that you’ve got quite an appetite for similar movies. If you are looking to enjoy more stories as exciting and as engaging as the one following the story of Ben Campbell, then you might want to read on. We’ve got a good list of movies like 21 that you could watch if you are looking for something else of similar challenge and intellectual depth.

Many times, movies like this can feel quite insulting to the audience. The joy of 21, though, is that it avoids any of these problems. What, though, might be a good similar film?

1. The Gambler

2. Vantage Point

3. Pain and Gain

4. Eagle Eye

5. Paranoia

6. Wall Street Money Never Sleeps

7. Need for Speed

8. Limitless

9. Catch me if You Can

10. Casino Jack

#1 The Gambler

A good place to start for many people would be the 2014 movie, The Gambler. It follows the story of the 1974 film of the same name, and builds on many of the same ideas. The remake, which stars Mark Wahlberg in the lead role, is a very interesting movie. It follows the story of Jim Bennett, a literature professor who is very much a self-destructive problem gambler.

The film centres around him getting into around $240k of debt to an underground gambling ring. He also owes $50k to a loan shark of some repute. With a week to get the money together or face murder, this high-stakes movie shows us just how desperate we’ll become to try and save ourselves and avoid the ultimate punishment.

#2 Vantage Point

Though not fully similar, 2008 political thriller Vantage Point is almost certainly worth looking into. It’s an interesting story that follows an attempt to assassinate the President of the United States. The story is taken from numerous different perspectives and points of view, hence the name of the movie in the first place.

We see a lot of events take place in the movie, with a lot of back and forth that can, at times, get a bit confusing. However, the movie does a good job of making you doubt what is the truth and what is not the truth throughout the movie, with various events that take place all carrying important distinctions and suggestions from one side to the next. Therefore, it’s one that keeps you guessing right to the end.

#3 Pain and Gain

This dark comedy is one that may not be for everyone, but it’s got a bit of a cult following for numerous reasons. It follows the story of a gym owner in 1990s Miami who wants to try and bring in more cash – so he turns to extortion in a bid to make a quick buck. To do that, he gets in Paul and Adrian, a pair of powerhouse musclemen who can do his bidding for him.

However, they struggle to make things go as they had intended until they manage to snag a business known as Victor Kershaw. When they manage to get Kershaw to hand over all of his assets, Kershaw eventually escapes. The law, though, aren’t too keen on his story. Can he get back what is his?

#4 Eagle Eye

When you are in the mood for a bit of deceit and espionage, 2008 thriller Eagle Eye is a good place for you to start. It’s a highly popular movie with a huge amount of excitement taking place during each scene. It follows the plot of two people who have to go on the run together, having received a mysterious phone call that tells them both they are being tracked and watched.

It’s quite an interesting one, and manages to follow a story that very quickly escalates. From the tragedy of a funeral to the mystery of how one character manages to be in possession of $750,000 and all manner of illegal items, the story soon evolves into a full-blown drama that keeps the excitement flowing throughout the entire plot.

#5 Paranoia

2013 release Paranoia is a good one to watch if you enjoy seeing a bit of espionage going on the backgrounds. It’s about Adam Cassidy, a rising name in the global tech industry. A mistake that he makes, though, could cost his reputation and his ability to continue moving up the ladder. In a bid to make up for his error, though, Cassidy is forced to enter into the world of corporate espionage, working as a spy for his current boss, Nicolas Wyatt.

Wyatt asks him to spy on Jock Goddard, a former partner of Wyatt. However, he soon gets to see first-hand just how far both will go to protect themselves: and the shocking consequences.

#6 Wall Street: Money Never Sleeps

Wall Street has been a fascination for many of us for large portions of our lives. A deeply exciting location that seems to drive much of the success and failure of the entire business world, Wall Street is almost legendary. The problem with Wall Street, though, is perfectly showcased in the 2010 released by Oliver Stone

It follows up on the 1987 release, Wall Street, and is a fantastic watch. It’s one that takes place two decades after the first movie, and follows the story of Gordon Gekko, a reformed antihero who is trying to make up for lost time with his family – especially his daughter. It’s a fun film watch, and one that sows us the importance of relationships – even to those at the top.

#7 Need for Speed

2014 thriller Need for Speed is based on the popular video game series of the same name. however, it’s a fun and exciting story that follows Tobey Marshall, a street racer with very few limits. He joints a cross-country race as a means of making up for the death of his friend, who died at he hands of a fellow racer named Dino Brewster.

While the film isn’t going to be for everyone, it’s got enough twists and turns to offer something quite intriguing to petrolheads. Probably the kind of film for a certain kind of audience, but something that everyone could get an enjoyable enough watch from.

#8 Limitless

Limitless is a hugely popular film released in 2011 that is based on the book, The Dark Fields. It’s a highly energising story, and one that shows us how Edward Morra, a writer who is having serious issues with creativity, overcomes his problem with the help of a pill. The pill, known as NZT-48, gives him the ability to maximise his brain power and to give him the chance to move his life to a whole new tier of success.

However, as you might imagine, things don’t quite go so smoothly as that. The film follows vast changes in how we Morra lives, and the consequences of the tool he is using to help propel himself to such incredible heights of artistry and creativity. Definitely a film that you should take the time to see if you enjoy the high-stakes nature of the previous movies.

#9 Catch Me If You Can

A hugely popular film for many reasons, 2002 release Catch Me If You Can should be very high up on your list of movies to watch. It follows the story of Frank Abignale Jr. who manages to be everything from an airline co-pilot to a doctor and a lawyer all before the age of 18. A deceptive mastermind, the movie follows the stories of a man who was able to make forgeries of just about anything.

The Steven Spielberg classic is probably one of the most enjoyable films in the genre; a true ode to the days when a bit of roguery could help you to manage just about anything. A truly spectacular watch, and one that reminds us just how ambitious some people can be.

If you want to watch a movie with twists and turns but also a fairly high feelgood factor, this is the place to start.

#10 Casino Jack

If you are a fan of the high stakes nature of 21, then you will enjoy Casino Jack. The 2010 comedy-drama follows the career of Jack Abramoff, a D.C. lobbyist and business mind. He was involved in a major US corruption scandal that led to convictions for major White House officials, including a series of congressional staffers and lobbyists.

Abramoff himself was convicted of fraud and conspiracy, as well as tax evasion, as well a trading expensive gifts, sports trips, and even food for political assistance. The story shows us just how excessively ambitious such people can be, and how there really are no limits as to where a lobbist will go if they think it could get them what they want.

If you really like the genius aspect of the movie, then you are going to love our list of movies about geniuses (21 is mentioned) but there are some other great films included in there, that we are sure you will absolutely love.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2019 Harry Sheen


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      14 months ago

      Catch Me If You Can is a great movie! Enjoyed your top 10 list! Keep up the good work!


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