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49 Best Woody Harrelson Movies to Watch Now

The Highwaymen
The Highwaymen

Woody Harrelson has had a long-running film career, and even if you feel like you have not watched a movie of his, you most probably have. The 61-year-old actor has a Primetime Emmy and two Screen Actor Guild Awards to his name! Alongside that, he also has had several honorable nominations for Academy and Golden Globe awards. From The People vs. Larry Flynt to Three Billboards Outside Ebbing, Missouri, Harrelson has not been disappointed ever.

Woody made his debut with the 1986 sports comedy “Wildcats”, after which he went on to be a part of numerous successful works. Harrelson became a widely known name after his work in the movie “The People vs. Larry Flynt”. The film accelerated his career in the industry and bagged him even more serious, meaningful roles in movies.

Since then, Woody Harrelson has become a well-known name in the movie industry. He has range, great immersion in roles, and an even greater camaraderie with whoever he works with.

If you are a Woody Harrelson fan or want to check out his work, here is a list of 49 Best Woody Harrelson Movies to Watch.

1. The People vs. Larry Flynt (1996)

The People vs. Larry Flynt is Woody Harrelson’s most applauded work, while also being a controversial movie under his name. Harrelson plays the role of Larry Flynt, who is a pornography publisher.

The People vs. Larry Flynt

The People vs. Larry Flynt

The movie shows the various phases of his life. These incidents revolve around the death of his true love (the rockstar Courtney Love gives a good performance), an assassination attempt against him which leaves him paralyzed, and lastly, a battle for free speech in the United States Supreme Court against a right-wing evangelist Jerry Falwell. Flynt, fortunately, wins this battle in the end.

Woody got his first Oscar Nomination through this film, but the controversial nature of the movie had been a problem for him. He had later admitted to being hurt by the backlash he had received from extreme feminist critics who disliked how the film glorified an exploitative man. For Harrelson, though, this film was an important statement regarding free speech.

2. The Sunchaser (1996)

The Sunchaser from 1996 by Michael Cimino harbors one of Harrelson’s best performances to date. Harrelson plays an oncologist who sets out on a spiritual journey with a teenager (Jon Seda) who had been a juvenile offender and is now dying of cancer.

Woody Harrelson in "The Sunchaser"

Woody Harrelson in “The Sunchaser”

Michael Cimino had expressed his idea of how he shows the actors to be, and that is, at their best performance. He admits to working towards making them look good so they can deliver worthy performances.

3. The Thin Red Line (1998)

The Thin Red Line by Terrence Malick in 1998 gives Woody Harrelson an important side role. It is based on the eponymous novel by James Jones. This movie came out after the director’s twenty-year break from movie direction and became a good work in no time. Malick has put together several big names for supporting characters, apart from Woody Harrelson, like Nick Nolte, Sean Penn, George Clooney, John Cusack, and so on.

Woody Harrelson as Sgt. Keck

Woody Harrelson as Sgt. Keck

Harrelson plays a platoon leader; the Sgt. Brian William Keck who stands out with his great work. The infantryman had bravely fought and died for the cause. This movie is about the skirmish at Guadalcanal during 1942-43.

4. The Edge of Seventeen (2016)

The Edge of Seventeen revolves around Nadine (Hailee Steinfield) who is a rather awkward high school student. When her brother starts dating her best friend, her life in her junior year becomes even more problematic. Woody Harrelson then comes in as a character of a mentor and teacher, Mr. Burner.

Hailee Steinfield and Woody Harrelson in The Edge Of Seventeen

Hailee Steinfield and Woody Harrelson in The Edge Of Seventeen

The movie is Kelly Fremon Craig’s first work as a director, and it has turned from an original miniseries to a full-fledged movie soon enough. Woody fits perfectly well as a guiding adult with rough edges of his own, something that he has excelled at playing over the years. The cast also involves Kyra Sedgwick, Hayden Szeto, Blake Jenner, and Haley Lu Richardson.

5. Out of the Furnace (2013)

Out of Furnace from 2013 is the enthralling story of the Baze Brothers (played by Christian Bale and Casey Affleck), who find themselves lost in the horrifying labyrinths of life. The setting of the film is a dark world full of crime and terror. Amidst this, Harrelson plays the role of a sociopathic criminal; truly an unforgettable performance.

Out of the Furnace

The director Scott Cooper had declared how much of a privilege he considers it to have gotten to work with this cast and be able to tell a captivating story through them. He considers the actors a great help in helping him realize his vision.

6. North Country (2005)

Woody Harrelson plays a more low-key character than his usual work in North Country, which came out in 2005. He is a lawyer who is helping women working in an iron mine IN Minnesota file complaints against the sexual harassment that they have been subjected to over time.

L-r: WOODY HARRELSON as Bill White and JEREMY RENNER as Bobby Sharp in North Country.

L-r: WOODY HARRELSON as Bill White and JEREMY RENNER as Bobby Sharp in North Country.

While his co-stars Charlize Theron and Frances McDormand received Oscar nominations for their roles and he did not, Harrelson still gives a wonderful performance as a lawyer cross-questioning the people who have been held accountable. North Country is a striking look into the suppressing patriarchal structure that hinders the professional lives of women. Woody Harrelson had expressed his interest in the film due to its importance in the world today; saying that the film makes a powerful political statement while also holding the entertaining side.

7. Defendor (2009)

Defendor is an underrated and canon superhero movie that audiences did not appreciate upon its release. However, Rotten Tomatoes reviews find a lot to like about this film. Woody Harrelson plays the superhero who takes upon the name of the Defendor as he fights crime at night.

Defendor

Defendor

Sadly, Defendor is a man with no real superpowers, which gives him the status of a vigilante rather than a superhero. Defendor’s character can be found similar to that of Rainn Wilson in “Super,” where he is a delusional man taking on the persona of a superhero to fight crime. We also see Kat Dennings, Elias Koteas, and Sandra Oh in the movie.

8. A Prairie Home Companion (2006)

A Prairie Home Companion from 2006 brings together a star-studded cast featuring the likes of Meryl Streep, Tommy Lee Jones, and, most importantly, Woody Harrelson. The director Robert Altman completed this film only a few months before his demise, and it serves as a proper farewell to the excellent filmmaker even to this day.

A Prairie Home Companion

A Prairie Home Companion

The plot follows a radio talk show that still is popular in the time of television. Altman takes great pride in working with star-studded casts, admitting that he is only then able to experiment and bring out something productive, all this while also learning in the process.

9. The Messenger (2009)

Woody Harrelson’s supporting role in the movie The Messenger in 2009 had earned him his second Oscar Nomination as Best Supporting Actor. The film is about an alcoholic army officer whose job requires him to deliver the news of the demise of the soldiers killed in action to their respective families.

Woody Harrelson in "The Messenger"

Woody Harrelson in “The Messenger”

The Orlando Sentinel had put popular thought into words by terming Harrelson’s performance as one delivering great emotional impact; very well making the role one of the best in his film career, something which most definitely deserved recognition from Oscars. Harrelson describes his character in the film as highly enraged and someone who keeps all of that rage under wraps.

10. Solo: A Star Wars Story (2018)

Solo is a side story set in the diverse Star Wars universe, throwing light as a prequel into the early days of Han Solo. The story is about a heist mission that can potentially be dangerous, all while focusing on several of Han Solo’s trademarks.

Solo: a Star Wars Story

Solo: a Star Wars Story

Instead of Harrison Ford in his iconic character, we see Alden Ehrenreich playing the same character. Additionally, Donald Glover plays Lando Clarissian and Joonas Suatomo plays Chewbacca. Harrelson has been given the role of Tobias Beckett, who is a member of the Crimson Dawn crime syndicate. Beckett also later acted as a mentor figure to Han Solo. The fatherly role is done justice to by Woody Harrelson well.

11. The Hunger Games Mockingjay: Part 1 (2014)

The Hunger Games had a two-part movie series by the names Mockingjay 1 and 2. The first installment in the series introduces the beginning of the end, without really introducing you to the end. While the movie is the lowest-ranked entry for the franchise on Rotten Tomatoes, it still set a considerable record at the box office when it came out in 2014.

Woody Harrelson in Mockingjay 1

Woody Harrelson in Mockingjay 1

Since Woody Harrelson plays Haymitch Abernathy, he reprises his role as the skeptical and alcoholic trainer. We also see the rest of the cast; Jennifer Lawrence, Liam Hemsworth, Elizabeth Banks, Stanley Tucci, Donald Sutherland, Jeffrey Wright, and the late Philip Seymour Hoffman reprising their roles.

12. The Hunger Games Mockingjay: Part 2 (2015)

Mockingjay 2 also did quite similarly to its first installment with the critics. Even so, the series was an overall success. Mockingjay did have quite lower box office collections, though. The sequel to the 2014 movie came out in 2015 and continues the story right where it was left off. The love triangle between Katniss, Peeta, and Gale is also finally resolved in this movie.

Woody Harrelson in Mockingjay 2

Woody Harrelson in Mockingjay 2

13. A Scanner Darkly (2006)

A Scanner Darkly uses rotoscope animation (where live-action footage has been animated) to narrate a peculiar science fiction plot. It is based on the novel of the same name, written by Philip K. Dick. The author has also created other book-to-movie works, such as “The Minority Report”, which became the Steven Spielberg film “We Can Remember it for you Wholesale”, starring Tom Cruise.

Woody Harrelson in "A Scanner Darkly"

Woody Harrelson in “A Scanner Darkly”

Keanu Reeves stars as an undercover cop that is living a double life. He soon loses his sense of identity after getting caught in a conspiracy revolving around a drug that has got its hold on the public. Woody Harrelson and Robert Downey Jr. have supporting roles as addicts of the drug. They spent the majority of the plot being tipsy and having several comedic moments of their own. The animation has been a result of great hard work, given hours and hours go into producing a minute of the film.

14. Kingpin (1996)

While Kingpin from 1996 is also a sports comedy, it did not gross as high as White Men Can’t Jump did during its time; even so, it is still an enjoyable movie starring Woody Harrelson. On top of that, the movie only gained popularity in the coming years when it even amassed a cult following.

Kingpin

Kingpin

The movie is primarily concerned with ten-pin bowling. Harrelson gives a surreal performance as an ex-professional bowler who is now an alcoholic. He then becomes the manager of an Amish bowler (Randy Quaid). Harrelson displays great camaraderie even here, and Bill Murray as a rival bowler hits up to the mark. The film is amongst the most entertaining on this list and worth checking out.

15. Doc Hollywood (1991)

Doc Hollywood was one of the earliest movies in Woody Harrelson’s film career. When it started, he was still starring in the show “Cheers’ while he was in this film. Ben Stone (Michael J. Fox) is a young doctor who is on his way to appearing for an interview that can get him a profitable job as a plastic surgeon in Beverly Hills. On the way, he ends up in a car accident and is compelled to live in a small town.

Woody Harrelson in Doc Holllywood

Woody Harrelson in Doc Hollywood

Lou (Julie Warner) is his lover, who would rather he continues to stay in the smaller town instead of going to Beverly Hills. Woody Harrelson stars as Hank Gordon, a resident in town who has romantic feelings for Lou. The movie has been adapted from the book “What? Dead Again?” by Neil B. Shulman. The movie is also liked by critics well.

16. War for the Planet of the Apes (2017)

War of the Planet of the Apes is the third movie from the “Planet of the Apes” trilogy. It is widely believed by the critics of the movie that Woody Harrelson’s role in it as “The Colonel” is a kind of homage to the character of the Colonel in “Apocalypse Now”, played by Marlon Brando.

Harrelson’s Colonel is an extremely mentally unstable man who is trying to forcefully remove the apes from their land, where they are now peacefully living. The character is played brilliantly and realistically, thanks to Woody’s expertise. He does well at recreating Marlon Brando’s work.

Woody Harrelson as "The Colonel"

Woody Harrelson as “The Colonel”

17. The Man from Toronto (2022)

One of the latest additions to Woody Harrelson’s filmography is “The Man from Toronto“. The film revolves around Teddy Jackson (Kevin Hart), who is an innocent but clumsy man, always getting himself into trouble or creating it for others. Woody Harrelson appears in a bolder role as an assassin termed the “Man from Toronto”. The two eventually cross paths due to Teddy’s carelessness in locating an AirBnB for himself and his wife. What follows next is an utter state of chaos.

Kevin Hart and Woody Harrelson in "The Man From Toronto"

Kevin Hart and Woody Harrelson in “The Man From Toronto”

18. Triangle of Sadness (2022)

Woody Harrelson’s latest movie, in 2022, also achieved success. It received accolades and a standing ovation of 8 minutes at the Cannes Film Festival. The story is about the models Carl and Yaya, who are exploring the world of fashion while also exploring the boundaries of their relationship. They get invited to a luxury cruise ship with rich passengers.

Woody Harrelson in "Triangle of Sadness"

Woody Harrelson in “Triangle of Sadness”

The ship is soon met with the fate of sinking, and the survivors are stranded on an island. Woody Harrelson plays the ship’s captain.

19. EDtv (1999)

EDtv is one of the few Woody Harelson movies that have sat really well with the critics on Rotten Tomatoes but were not as enjoyed by audiences, sadly. In the movie, Ed (Matthew McConaughey) is a man whose life becomes a television production, or rather, a 24/7 running proto-reality TV series, when he agrees to have a camera team record his everyday life. Ray (Woody Harrelson) is Ed’s buffed but quite dim brother who wants the spotlight that his brother is constantly under all to himself instead.

EDtv

EDtv

The movie seems similar in theme to the Jim Carrey starrer “The Truman Show”, which came out a year earlier than it did. While The Truman Show was more inclined towards showing the idea of a man’s distorted reality, EDtv is more inclined in being a comedic piece.

20. White Men Can’t Jump (1992)

Contradictory to the title, Harrelson is a white man in the movie who can, in fact, jump. He is a hustling basketball player who starts playing street games to earn money so he can pay off his gambling debts. He gets involved in games with players who believe that he cannot play because he is a white man.

White Men Can't Jump

White Men Can’t Jump

This movie acted as both a hit film and a transitional phase in his film career. At this time, he was making a move from being a TV actor in the show “Cheer” to having a major career in movies and his way to stardom. Harrelson does great in this movie alongside co-stars Wesley Snipes and Rosie Perez. The movie has just the right amount of humor to entertain you. It is also being said that a movie remake is currently in the works!

21. Wilson (2017)

Wilson is the story of a neurotic and funnily honest middle-aged man named Wilson (Woody Harrelson). He is united with his estranged wife, Pippi (Laura Dern), after seventeen years. He is soon more than delighted to hear that he has a teenage daughter (Isabella Amara) who he has never met. He makes it his purpose to set out in an attempt to unite and connect with her after all these years.

Woody Harrelson and Laura Dern in Wilson

Woody Harrelson and Laura Dern in Wilson

22. LBJ (2016)

LBJ is the result of a collaboration between Woody Harrelson, director Rob Reiner, and writer Joey Hartstone. However, the work has not been much applauded by either the critics or the audience. Woody Harrelson plays the role of Lyndon B. Johnson, who succeeded John F. Kennedy when he was assassinated.

LBJ

LBJ

The movie begins before the assassination takes place and essentially deals with the aftermath of the event. It also highlights how Lyndon B. Johnson dealt with the 1960s civil rights movement. The role of John F. Kennedy is done by Jeffrey Donovan, while Michael Stahl David plays his brother Bobby Kennedy.

LBJ’s wife, Lady Bird Johnson, is played by Jennifer Jason. We also see Richard Jenkins and Bill Pullman in the roles of some important senators during that time. Some critics find Woody Harrelson a case of miscasting in his role as LBJ but cannot deny that the actor is “spicy” enough to keep the viewer’s attention after all.

23. Welcome to Sarajevo (1997)

Welcome to Sarajevo has been critically acclaimed but still underrated over the years. Woody Harrelson is seen as Jimmy Flynn, a popular American journalist who is currently covering the war taking place in Bosnia and Herzegovina, the countries formed upon the dissolution of Yugoslavia.

Woody Harrelson in "Welcome to Sarajevo"

Woody Harrelson in “Welcome to Sarajevo”

Jimmy Flynn is a rather egoistic character who is of self-proclaimed significance. He feels that no one has heard of Yugoslavia, but everyone knows him. Which he feels gives him the right to cover the story of circumstances in that place in any manner he sees fit. The movie is a closer investigation of how limited journalist detachment is. Jimmy Flynn finds himself on a quest to rescue orphans out of the war zone.

24. The Duel (2016)

The Duel from 2016 is set in a town called Helena. The place has recently had a series of unexplained deaths among the people. A Texan ranger David Kingston is soon sent out to investigate the happenings. Woody Harrelson plays Abraham Brant, the preacher and mayor of the town. Abraham had killed Kingston’s father in a “duel” knife fight back in 1866 and now keeps the town under his fearful grip. Kingston infiltrates the town by hiding his identity and sneakily tries to uncover the truth.

The Duel

Liam Hemsworth and Woody Harrelson in The Duel

25. Venom: Let There Be Carnage (2021)

Venom: Let there Be Carnage garnered even more critical acclaim, and audience approval than its prequel movie did in the theatres in 2018. Tom Hardy plays the roles of both Eddie Brock and Venom, giving him a double role. Woody Harrelson also has a similar double role, playing both Kasady and Carnage. The movie is one of Harrelson’s most recent works in the movies. He was shown briefly in the first film as the first “Venom”, and he returns this time as a villain in the sequel.

Woody Harrelson in Venom 2

Woody Harrelson in Venom 2

Interestingly, critics have called the first installment in the Venom series “toxically dull”, but termed the second movie as rather “intoxicating”. The additional humor in the 2021 movie adds to the plot’s charm, making it widely liked.  

26. Three Billboards Outside Ebbing, Missouri (2017)

Woody Harrelson received his third Oscar nomination for his role in Three Billboards Outside Ebbing, Missouri, where he again has teamed up with the director Martin McDonagh. The story revolves around a mother (Frances McDormand) who obsessively campaigns by hiring three billboards to bring justice to her daughter’s killer and rapist.

Three Billboards Outside Ebbing, Missouri

Three Billboards Outside Ebbing, Missouri

Harrelson plays the role of the Sheriff that McDormand hounds so she can locate the killer. While his co-star Sam Rockwell got the award for Supporting Actor for the movie, Woody Harrelson’s stable portrayal of a man who has cancer is one of the most unforgettable things about the movie.

27. Triple 9 (2016)

Triple 9 is a feature film by John Hillcoat, who also made the post-apocalyptic movie “The Road”. The movie revolves around several corrupt cops and criminals who set up a heist that involves the pre-planned murder of another police officer. Soon enough, local gangs and the Russian mob are all part of the greater crime, making this movie even more thrilling.

Triple 9

Triple 9

Woody Harrelson plays the role of one of the police officers working in the heist amidst a great cast including Kate Winslet, Gal Gadot, Casey Affleck, Chiwetel Ejiofor, Norman Reedus, Michael K. Williams, Clifton Collins Jr., Aaron Paul, and Anthony Mackie.

28. The Highwaymen (2019)

While the opinion is subjective and fans all have different views on which movie can be the finest from Woody Harrelson’s career, a wide bunch of them believe that The Highwaymen is the best movie that stars the actor. The film is a biographical work with crime and drama as its main genres. The story is about Maney Gault (Woody Harrelson) and Frank Hamer (Kevin Costner), the less talked about and brave Texas Rangers who brought Bonnie and Clyde to justice in the 1930s.

The Highwaymen

The Highwaymen

The Highwaymen is a change in the narrative that often favors the criminals themselves. While not as stirring as the Bonnie and Clyde movie from 1967, the new perspective is outright refreshing in honoring an unsung part of American History.

29. Zombieland (2009)

Zombieland is one of the highest-grossing films at the box office that starred Woody Harrelson, making it one of his biggest successes. The film is set in a post-apocalyptic world where zombies have taken over the planet, making it a comedic horror movie. It balances really well between intensely gore-centric scenes and hilarious comedy now and then, something that never stops throughout the film.

Zombieland

Zombieland

In recent television and film creations that revolved around zombies, the latter have been defeated and killed. But this movie takes a different stance and is different from the other works in its genre. Woody Harrelson plays the role of gun-donning Tallahassee; Jesse Eisenburg plays the neurotic Columbus; Emma Stone plays the strong-willed Wichita. There is also a Bill Murray cameo to look forward to. Harrelson was termed as having a great time as humankind’s “last best hope” by the Chicago Tribune.

30. 2012 (2009)

2012 is a movie revolving around the collective hysteria of the world in believing that the world will end on December 21st, 2012. The rumors flew from the talk of planetary alignments and mentions in the Mayan Calendar. We all know none of that had come true, but the fear amongst people was so strong that even NASA had to publish an article to debunk the myth.

Woody Harrelson in 2012

Woody Harrelson in 2012

2012 shows John Cusack in the role of a father trying to save his family in times of disaster. The film shows floods and earthquakes striking the world. Harrelson plays a small role as a crackpot conspiracy theorist called Charlie Frost.

31. The Hi-Lo Country (1998)

The Hi-Lo Country is based on a Max Evan novel. It is a look into the mythology of cowboys in a continuously advancing world. Woody Harrelson and Billy Crudup star as two best friends who come back home, only to find out that the values they held so dear since childhood now face the threat of extinction.

The Hi-Lo Country (1998)Shown from left: Billy Crudup, Woody Harrelson

The Hi-Lo Country (1998)
Shown from left: Billy Crudup, Woody Harrelson

The movie won the Silver Bear for Best Director at the Berlin Film Festival. Stephen Frears, the director, has described the main characters as being cowboys at a strange time; mentioning that they did not have anything to do even when they were two tough men.

32. Kate (2021)

Kate is the less talked about Netflix movie from 2021 that gave Mary Elizabeth Winstead a good chance to portray their talent. Sadly, the movie has not gained a lot of critical acclaims. The story is about Kate, an efficient assassin in Tokyo. She is soon infected with a radiating poison which leaves her with just 24 hours. In the given time, she has to find out who did it and seek revenge.

kate

kate

Ani is a young girl who unexpectedly gets involved in Kate’s mission without realizing her being responsible for her father’s death. Harrelson here plays the role of Kate’s handler and mentor. The action scenes have mostly been really good in the movie too.

33. Indecent Proposal (1993)

Adrian Lyne once again comes forward with an unconventional and controversial film after “Fatal Attraction”. We see Woody Harrelson play Demi Moore’s Husband in Indecent Proposal. The couple is going through financial issues and decides to go to Las Vegas so they can gamble their way through their constraints. After all of their gambling attempts fail, the couple finds deeper disappointment.

Woody Harrelson and Demi Moore in "Indecent Proposal"

Woody Harrelson and Demi Moore in “Indecent Proposal”

However, they are soon met with Robert Redford, who plays a billionaire in the movie. He offers the couple one million rupees in exchange for sleeping with Demi Moore. After a lot of debate and discussion, the two accept the billionaire’s questionable offer. Harrelson is soon consumed by jealousy and realizes what he has done.

Woody Harrelson excellently carries the emotional impact of the movie by being a man who soon understands that money cannot buy happiness. His character in the movie is also the one carrying the plot by the end.

34. Now You See Me (2013)

The first installment in the Now You See Me movie series, which came out in 2013, has done remarkably well to its successor. The magician crime movie was alright with the critics and also became a crowd-pleaser in no time. Some critics were amazed by the performances given by some big names such as Mark Ruffalo, Dave Franco, Jesse Eisenberg, Michael Caine, Morgan Freeman, Melanie Laurent, Isla Fisher, and of course, Woody Harrelson. Others found it embedded with some plot holes.

WOODY HARRELSON (center) stars in NOW YOU SEE ME

WOODY HARRELSON (center) stars in NOW YOU SEE ME

The story is that of an FBI agent who attempts to get his hand on a group of magicians that are known as the “Four Horsemen”. They have a penchant for looting banks as an ensemble of their Las Vegas magic act. There are a lot of unexpected twists in the plot to look forward to as well.

35. Now You See Me 2 (2016)

The sequel to Now You See Me continues where the last movie ends. The Four Horsemen return to resume their purpose of the heist, and we see the same cast, including Woody Harrelson reprising their roles. Daniel Radcliffe and Lizzy Caplan join the main cast this time as well. The movie did not do as well as its prequel, unfortunately.

Woody Harrelson in Now You See Me 2

Woody Harrelson in Now You See Me 2

36. Anger Management (2003)

Anger Management has not been the most-liked film by critics. Even so, the Adam Sandler and Jack Nicholson starrer has done quite well with the people as a comedic movie. Dave Buznik (Adam Sandler) is a timid businessman for a company in New York that makes clothes for pets. Upon a misconstrued violent dispute that he has on a flight, he is immediately sent to an anger management class that is mandated by the court.

Woody Harrelson as Gary "Galaxia" in "Anger Management"

Woody Harrelson as Gary “Galaxia” in “Anger Management”

The classes are run by the psychotic Dr. Buddy Rydell (Jack Nicholson). Woody Harrelson appears in the supporting role of the guard named Gary, who also works as a prostitute in drag by the name Galaxia.

37. Natural Born Killers (1994)

Natural Born Killers by Oliver Stone 1994 is based on the novel by Quentin Tarantino. The movie is the most controversial part of Woody Harrelson’s filmography. The film came not long after the murder of Nicole Simpson and Ron Goldman by O.J. Simpson, who was Nicole’s ex-husband. The movie significantly ate off of the popular fascination of people and the media with criminals and true crime stories. The movie, over time, has become a cult classic.

Natural Born Killers

Natural Born Killers

Woody Harrelson and Juliette Lewis star as a married couple, Mickey and Mallory being the latter era “Bonnie and Clyde”. The two go on a murdering spree, which gains them public recognition and notoriety. What is strange is that the film very creepily predicts the Columbine High School murders, which happened a few years later. The Columbine assassins followed in similar footsteps as those in the movie and had a hungry media lap up the news of their murders and actions.

38. Wag the Dog (1997)

Barry Levinson’s Wag the Dog from 1997 gives Woody Harrelson a smaller role but still an impactful one. He plays Sergeant William Schumann, who is a former soldier that turned insane. Upon his death, the plans for the contingent made by the President’s team are unfortunately sabotaged.

Woody Harrelson on the set of "Wag the Dog"

Woody Harrelson on the set of “Wag the Dog”

Harrelson does not have a lot of screen time in this movie, but he proves that he can give a compelling and memorable performance even in the little scenes he does get to appear in. The film holds significance even in today’s time, subtly criticizing several political mechanisms. The issues addressed in the movie are also extremely serious.

39. The Glass Castle (2017)

The Glass Castle is a compelling, excellent biographical drama that adapts Jeannette Walls’ popular memoir in which she reminisces her life as a child in a poverty-stricken environment. Woody Harrelson stars in the deep role of a father who attempts to strike a balance between his desires and his responsibilities towards his family.

Glass Castle

Glass Castle

Harrelson recalled how the movie covers several different time frames and goes back and forth on them. He gives the director Destin Daniel Cretton the credit for being able to make it all work and having it all come out so seamlessly.

40. Money Train (1995)

Money Train reunited Woody Harrelson and Wesley Snipes after they starred in “White Men Can’t Jump” together. The two play a pair of cops in the city of New York and also happen to be foster brothers. When one of them loses their job, they turn to robbing a lot of money. It is now up to the other brother to take care of their brother, so things do not go sideways. Money Train is not widely applauded, but it is called better than the action films contemporary to its release.

Money Train

Money Train

41. No Country for Old Men (2007)

No Country for Old Men 2007 has won four Oscars; Best Picture, Best Director, Best Adapted Screenplay, and the Supporting Actor Award for Javier Bardem. The movie is based on the book by Cormac McCarthy. Javier Bardem plays a killer who is killing anyone and everyone who crosses his path while he stumbles from place to place.

Woody Harrelson in No Country For Old men

Woody Harrelson in No Country For Old men

Woody Harrelson has a supporting role in the film, playing an operative hired to bring down this killer. Even amongst a great cast ensemble, Harrelson has managed to stand out. The film had also been one of his most rewarded and applauded works during that time. After Javier, he is the most interesting character in the film.

42. Seven Pounds (2008)

Seven pounds is yet another movie that was enjoyed more by the audiences than it was by the critics who called it “nonsensical”. However, the performances by Will Smith and Rosario Dawson are great and worth checking out. Will Smith plays Ben Thomas, who is a mysterious man with secrets of his own. He decides to change the lives of seven strangers for unknown reasons. Woody plays one of these strangers, Ezra.

Woody Harrelson and Will Smith in Columbia Pictures' drama SEVEN POUNDS.

Woody Harrelson and Will Smith in Columbia Pictures’ drama SEVEN POUNDS.

43. Transsiberian (2008)

Transsiberian is a 2008 thriller by Brad Anderson. The plot takes place on an express train that runs between China and Moscow. Woody Harrelson and Emily Mortimer play the role of missionaries. The movie acts like a strange version of Agatha Christie’s crime thriller “The Murder on the Orient Express”. Harrelson impresses with a brilliant performance that surely will keep you on the edge of your seats.

TRANSSIBERIAN, center: Woody Harrelson, Emily Mortimer, 2008.

TRANSSIBERIAN, center: Woody Harrelson, Emily Mortimer, 2008.

Harrelson’s co-star Kata Mara applauds him by calling him a fearless person in front of the camera. She calls him a person with an experimental nature who does not shy away from trying new things while acting. She also does not fail to acknowledge the great contribution he has in the film.

44. The Cowboy Way (1994)

The Cowboy Way in itself is a rather average movie, but not Harrelson. He plays one of his most comedic and intriguing roles. The story is about two Rodeo stars that are traveling across the country in search of their missing friend.

Woody Harrelson in The Cowboy way

Woody Harrelson in The Cowboy way

The script remains bland for the most part, yet Harrelson steals the show with his good comic timing and great likeableness seen throughout the movie. The iconic and physically comedic scene starring with Harrelson naked with an oddly placed cowboy hat comes from this movie.

45. Semi-Pro (2008)

Semi-Pro is a sports movie based in the 1970s and on the Flint, Michigan Tropics. The team was an ABA basketball one that had dreams of merging with the NBA. The team involves Clarence (Andre 3000), the best player, and Monix (Woody Harrelson), who has played at a professional level for the Boston Celtics.

Semi-pro

Semi-pro

46. Rampart (2011)

Putting together the talent of Woody Harrelson, Steve Buscemi, and Sigourney Weaver is the 2011 drama movie Rampart by Oren Moverman. The plot is based on the Rampart Scandal of the ’90s. It follows a corrupt police officer (played by woody Harrelson). The movie in itself is not up to the mark. Woody’s performance is the only good thing about it, and his performance even gained him greater critical acclaim.

Rampart

Rampart

The actor and the director’s friendship had been through a rough patch due to the contrasting opinions they both had about the final cut. Fortunately, the two were able to reach some conclusion and decided not to base their friendship on such an issue.

47. Shock and Awe (2017)

Shock and Awe are set when George W. Bush was the President and how the U.S. military was preparing to invade the Middle East to find Saddam Hussein, to put an end to his weapons of mass destruction.

Shock and awe

Shock and Awe

Woody Harrelson stars as Jonathan Landay, a journalist who is suspicious of the motives that go behind the invasion. The director Reiner also starred in the movie and is responsible for making several critically acclaimed movies in the past.

48. Seven Psychopaths (2012)

Harrelson has his first collaboration with the writer, playwright, and screenwriter Martin McDonagh as one of the psychopaths in the movie “Seven Psychopaths” which came out in 2012. The film follows the stories and exploits of seven psychopathic people, taking its time to familiarise you with each of them.

Seven Psychopaths

Seven Psychopaths

Woody Harrelson plays the role of Charlie Costello. Charlie is a violent gangster who is out to get the people who have dog-napped his beloved Shih Tzu. Harrelson does great in playing these unhinged and out-of-the-box characters with a certain depth to them. The movie makes for a great crime thriller too.

49. She Hate Me (2004)

Jack Armstrong (Anthony Mackie) is a high-paid executive at a biotechnology company. However, Armstrong is an honest man who can blow off the covers. This puts him on the radar of his boss, who fabricates evidence to fire him.

Woody Harrelson in "She Hate Me"

Woody Harrelson in “She Hate Me”

After he gets fired, he finds himself taking up a strange profession that requires him to impregnating wealthy lesbians for $10,000 each. One of the women is also his former fiancée, who came out at the end of their relationship.

Woody Harrelson has a minor supporting role as Armstrong’s superior in his corporate job.

Also Read: 15 Shows like Dahmer on Netflix That Will Stun You

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I am an intensive entertainment consumer. My interests lie in all genres of anime, movies and shows!

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