MIDWAY GENTLEMAN

20 Movies Every Man Should Watch In Their Life

In today's article, I will list twenty iconic movies that all men should watch at least once. I tried to mix different genres and not focus on one or another. From animated to action movies, you'll find some of the most iconic films in this list.

We could create a list twice the size of this with ease, but we try to strict this article to the best twenty movies every man should see. We are currently working on the following article, where we list another twenty iconic pieces. Stay tuned for that. Now, enjoy the first twenty masterpieces.

1. The Wolf of the Wall Street, 2013

The movie is a must for everyone working in sales or trading. While we have many concerns with how Jordan Belfort ran his business and family life, we cannot deny he was an excellent salesman and still is today. The movie is full of jokes and things to learn – and of course, a lot of graphic content, which might be too much for some.

Leonardo DiCaprio in The Wolf of Wall Street
Leonardo DiCaprio in The Wolf of Wall Street

2. The Gentlemen, 2019

The Gentlemen is one of the best new gangster movies – made by the one and only Guy Ritchie. While it is relatively new on the list, it has already become a cult movie in the gentleman and men’s lifestyle community. Pour your best scotch and enjoy this movie filled with action and humor.

Matthew McConaughey In Patterned Suit Afternoon Tea The Gentlemen 2019
Matthew McConaughey as Mickey Pearson in © The Gentlemen, 2019

3. The Intern, 2015

After two 18+ movies on the list comes a family-friendly movie. The Intern was one of my favorite films when it hit the cinemas. It represents the modern generations and the way they interact with each other. You can learn a lot from this movie about dignity, style, and class. It is a fun and motivational film that can be the perfect choice for couples, families, and even solo movie watchers.

Robert De Niro and Anne Hathaway in 'The Intern'
Robert De Niro and Anne Hathaway in ‘The Intern’

4. Wall Street

Whether you are watching the original 1987 movie or the 2010 sequel, you will enjoy it the same. For example, I saw the sequel first, and although I didn’t understand a few things, it was an excellent movie, and once I saw the original, I understood everything. You can learn a lot about how businesses and the stock market work from this timeless classic.

Michael Douglas as Gordon Gekko in 'Wall Street: Money Never Sleeps', 1987
Michael Douglas as Gordon Gekko in ‘Wall Street: Money Never Sleeps’, 1987

5. A Few Good Men, 1992

„You want answers? I want the truth! You can’t handle the truth!” A Few Good Men is an American legal drama and also a timeless classic. The plot follows the court-martial of two U.S. Marines charged with the murder of a fellow Marine and the tribulations of their lawyers as they prepare a case. The movie is full of lines you will remember for the rest of your life, like the one at the beginning of my paragraph.

Tom Cruise and Demi Moore in 'A Few Good Men'
Tom Cruise and Demi Moore in ‘A Few Good Men’

6. American Psycho, 2000

A controversial movie that has become a classic that all men have to see at least once. The film is about a wealthy New York City investment banking executive, Patrick Bateman, who hides his alternate psychopathic ego from his co-workers and friends as he delves deeper into his violent, hedonistic fantasies. The movie perfectly blends comedy with horror and thriller styles.

Christian Bale in American Psycho
Christian Bale in American Psycho

7. Scarface, 1983

Scarface is a 1983 American epic crime drama film directed by Brian De Palma and written by Oliver Stone. Loosely based on the 1929 novel of the same name and serving as a loose remake of the 1932 film, it tells the story of Cuban refugee Tony Montana (Al Pacino), who arrives penniless in Miami during the Mariel boatlift and becomes a powerful and remarkably homicidal drug lord.

Al Pacino as Tony Montana in Scarface
Al Pacino as Tony Montana in Scarface

8. Rocky Franchise

Rocky is an American sports drama franchise created by Sylvester Stallone, which began with the eponymous 1976 film and has since become a cultural phenomenon. The movies are centered on the boxing career of Rocky Balboa. The franchise has been expanded into various films, and with a total worldwide gross of $1.7 billion, it is currently one of the highest-grossing media franchises. Rocky is way more than a boxing movie franchise. The series inspired millions of kids and adults all around to globe to push harder in life and work on their goals to achieve them.

Sylvester Stallone in Rocky
Sylvester Stallone in Rocky

9. GoodFellas, 1990

Goodfellas is a 1990 American biographical crime film directed by Martin Scorsese, co-written by Nicholas Pileggi and Scorsese, and produced by Irwin Winkler. It is a film adaptation of the 1985 nonfiction book Wiseguy by Pileggi. Starring Robert De Niro, Ray Liotta, Joe Pesci, Lorraine Bracco, and Paul Sorvino, the film narrates the rise and fall of mob associate Henry Hill and his friends and family from 1955 to 1980. Goodfellas is a classic gangster movie that all men should watch at least once.

GoodFellas, 1990
GoodFellas, 1990

10. The Basketball Diaries, 1995

The Basketball Diaries is a 1995 American biographical crime drama directed by Scott Kalvert and based on an autobiographical novel by the same name written by Jim Carroll. It tells the story of Carroll’s teenage years as a promising high school basketball player and writer who develops an addiction to heroin. The movie stars Leonardo DiCaprio as Carroll, along with Bruno Kirby, Lorraine Bracco, Ernie Hudson, Patrick McGaw, James Madio, Michael Imperioli, and Mark Wahlberg in supporting roles. It is an enlightening movie that everyone should watch and learn from.

Leonardo DiCaprio in The Basketball Diaries
Leonardo DiCaprio in The Basketball Diaries

11. James Bond Franchise

„The name is Bond … James Bond.” Who wouldn’t know the iconic story of Brittain’s top spy? The movie franchise started with the 1962 movie Dr. No starring Sean Connery and portrayed by six others over the past 60 years. James Bond is a fictional character created by the British journalist and novelist Ian Fleming in 1952. The literary character appeared in a series of twelve novels and two short story collections written by Fleming and several continuation novels and spin-off works after Fleming’s death in 1964.

James Bond Dr. No – Featuring Sean Connery

12. Pulp Fiction, 1994

Pulp Fiction is in the top 10 best movies rated by IMDb, and I can clearly see why. Pulp Fiction is a 1994 American black comedy crime film written and directed by Quentin Tarantino, who envisioned it with Roger Avary. Starring John Travolta, Samuel L. Jackson, Bruce Willis, Tim Roth, Ving Rhames, and Uma Thurman. The movie tells several stories of crime in Los Angeles. If you like dark humor and the mentioned actors and actresses, you will love Pulp Fiction.

Uma Thurman Photographed for Pulp Fiction
Uma Thurman Photographed for Pulp Fiction

13. Rush, 2013

Rush is a 2013 biographical sports film centered on the rivalry between two Formula One drivers, the Briton, James Hunt, and the Austrian, Niki Lauda, during the 1976 motor-racing season. It was written by Peter Morgan, directed by Ron Howard, and starred Chris Hemsworth as Hunt and Daniel Brühl as Lauda. The movie perfectly portrays the intense rivalry between James Hunt and Niki Lauda. The film is full of action, fun, and drama. I recommend watching it to everyone whether they like Formula 1 or not.

Scene From © Rush, 2013
Scene From © Rush, 2013

14. Hacksaw Ridge, 2016

Hacksaw Ridge is a 2016 biographical war film directed by Mel Gibson and written by Andrew Knight and Robert Schenkkan, based on the 2004 documentary The Conscientious Objector. 

Andrew Garfield as Desmond Doss in Hacksaw Ridge
Andrew Garfield as Desmond Doss in Hacksaw Ridge

The film focuses on the World War II experiences of Desmond Doss, an American pacifist combat medic who, as a Seventh-day Adventist Christian, refused to carry or use a weapon or firearm of any kind. Doss became the first conscientious objector to be awarded the Medal of Honor for service above and beyond the call of duty during the Battle of Okinawa. If you like war movies or want to be inspired, it is a must-watch movie.

15. The Lincoln Lawyer, 2011

The Lincoln Lawyer is a 2011 American legal thriller film adapted from the 2005 novel by Michael Connelly. It is directed by Brad Furman, with a screenplay written by John Romano, and stars Matthew McConaughey as the titular lawyer, Mickey Haller. The film also stars Ryan Phillippe, Marisa Tomei, Josh Lucas, William H. Macy, and Bryan Cranston. This movie was one of the least known movies by Matthew McConaughey for me, and it was a total shocker when I saw it for the first time. It is filled with twists and was engaging from the first seconds to the last.

Matthew McConaughey in The Lincoln Lawyer, 2011
Matthew McConaughey in The Lincoln Lawyer, 2011

16. Steve Jobs, 2015

Steve Jobs is a 2015 biographical drama film directed by Danny Boyle and written by Aaron Sorkin. A British-American co-production, it was adapted from the 2011 biography by Walter Isaacson and interviews conducted by Sorkin. The movie covers 14 years (1984–1998) in the life of Apple Inc. co-founder Steve Jobs. Jobs is portrayed by Michael Fassbender, with Kate Winslet as Joanna Hoffman and Seth Rogen, Katherine Waterston, Michael Stuhlbarg, and Jeff Daniels in supporting roles.

Michael Fassbender as Steve Jobs
Michael Fassbender as Steve Jobs in © Steve Jobs, 2015

The movie shows the behind-the-scenes of three iconic keynotes from the revolutionary tech giant Apple, and it ends with the 1998 Keynote where Steve Jobs presented the iMac to the world. The movie portrays the mysterious life of Steve Jobs and how he returned to Apple after his resignation.

17. Inception, 2010

Inception is a 2010 science fiction action film written and directed by Christopher Nolan, who also produced the film with Emma Thomas, his wife. The film stars Leonardo DiCaprio as a professional thief who steals information by infiltrating the subconscious of his targets. He is offered a chance to have his criminal history erased as payment for the implantation of another person’s idea into a target’s subconscious. It is a complex movie that requires multiple watches to understand.

Inception 2010 Cover
Inception 2010 Cover

18. The Fight Club, 1999

Fight Club is a 1999 American film directed by David Fincher and starring Brad Pitt, Edward Norton, and Helena Bonham Carter. The movie is based on the 1996 novel by Chuck Palahniuk. Norton plays the unnamed narrator, who is dissatisfied with his white-collar job. He forms a “fight club” with soap salesman Tyler Durden (Pitt) and becomes embroiled in a relationship with a destitute woman, Marla Singer (Bonham Carter). Fight Club has many twists in its story, which makes it engaging throughout the entire movie.

Brad Pitt Featured in The Fight Club, 1999
Brad Pitt Featured in The Fight Club, 1999

19. Toy Story, 1995

You can argue why an animated movie is on the list, but Toy Story was a revolutionary movie when it came out and still is. This was the movie that put Pixar on the map and started an era of high-resolution animation movies. Whether you saw it as a child or with your children, Toy Story is a great movie not just for kids.

Toy Story Cover, © Disney
Toy Story Cover, © Disney

Toy Story is a 1995 American computer-animated comedy film directed by John Lasseter, produced by Pixar Animation Studios, and released by Walt Disney Pictures. The first installment in the Toy Story franchise. It was the first entirely computer-animated feature film, as well as the first feature film from Pixar. You can never be too cool to watch animated movies with your family.

20. Rain Man, 1988

Finally, a movie that I neglected for years. I always thought that Rain Man was a boring old movie, but I was so wrong. Rain Man is a 1988 American road comedy-drama film directed by Barry Levinson. It tells the story of abrasive, selfish young wheeler-dealer Charlie Babbitt played by Tom Cruise, who discovers that his estranged father has died and bequeathed virtually all of his multimillion-dollar estate to his other son, Raymond, played by Dustin Hoffman, an autistic savant, of whose existence Charlie was unaware. Charlie is left with only his father’s beloved vintage car and rosebushes. Valeria Golino also stars as Charlie’s girlfriend Susanna. It is an engaging movie that teaches a lot of empathy in life.

Dustin Hoffman and Tom Cruise in Rain Man
Dustin Hoffman (Left) and Tom Cruise (Right) in Rain Man

Endnote

The list could go on and on. There are still many movies I’d like to cover, but I leave some room for a future article. The 20 movies listed above are classics that every man should watch at least once in their life.

Keep on reading: 20 Bits of Advice Every Man Should Follow in Life: Tips for the Modern Gentleman

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