Wicked Good: Our Favorite Affleck and Damon Flicks

KC Frankenburger

Read Time 6 minutes

matt damon ben affleck
Matt Damon and Ben Affleck in “Good Will Hunting” from Miramax Films

Buckle up, folks! It looks like our favorite 90s BFFs are teaming up yet again, this time for the retelling of the true story of how one man gamed the McDonald’s Monopoly sweepstakes (for over a DECADE, y’all!).

When the in-depth tell-all story went live at the end of last month, a furious bidding war between studios erupted, which ended with Ben Affleck and Matt Damon holding the winning bid after joining forces along with their production company, Pearl Street Films. Now that these Bostonians are in possession of the rights, rumor has it that Affleck will direct and Damon will star, with the possibility of both of them appearing on screen. Personally? I can’t wait.

Now for a trip down memory lane. In celebration of this epic reunion, take a look below for a complete listing of all of our favorite Damon and Affleck pictures.

  1. Good Will Hunting – HBO

This list would not be complete without the film that made this duo pretty much unstoppable. Also starring Robin Williams and Minnie Driver, Good Will Hunting also earned the famous duo an Oscar for their screenplay.

  1. Argo

Speaking of the Academy Awards, Argo which was directed by and starring Ben Affleck, took home the award for Best Picture back in 2013.

  1. The Martian – FX | Fox  

Based on the book by novelist Andy Weir, The Martian stars Matt Damon and tells the story of Mark Watney, a scientist who is left behind during a manned mission to Mars, and must use his skills as a botanist and mechanical engineer in order to survive long enough to be rescued.

  1. Gone Girl – FX | Fox

This thriller starring Affleck, Neil Patrick Harris and an icy Rosamund Pike, was a huge hit back in 2014. The film is based on the mystery novel of the same name by acclaimed author Gillian Flynn.

  1. The Departed – Netflix  

Here, Damon plays a mobster who goes undercover as a cop during a volatile time in Boston. With an all-star cast, The Departed tops many viewers’ list of their favorite movies of all time.

  1. The Town

Written, directed by and starring Ben Affleck, The Town is the story of a group of ruthless bank robbers who take a young bank employee hostage during one of their raids. In the aftermath, when a member of the group, Doug (Affleck) begins to fall for the young woman, he may be putting them both at risk.

  1. The Talented Mr. Ripley – Starz | Epix

Directed by the late Anthony Minghella and starring Damon, Gwyneth Paltrow, Jude Law and Philip Seymour Hoffman, Ripley is a cautionary tale about a young man who takes an unhealthy obsession to unimaginable lengths.

  1. Dogma

One of my favorite films starring these two together, Dogma is a darkly comic religious tale: one of the search for Christ’s heir, and of two fallen angels (Damon and Affleck) who attempt to re-enter heaven without permission. While this film is not currently streaming, you can get a healthy dose of Damon and Affleck playing off of each other in the best way possible with this garage scene.

  1. Gone Baby Gone – Netflix  

Directed by Affleck and based on the crime novel by Dennis Lehane, Gone Baby Gone is a darkly gritty drama that follows two private investigators hired after a young girl goes missing from a rough neighborhood. The film stars Michelle Monaghan, Morgan Freeman, and Casey Affleck.

  1. Ocean’s Eleven

In this remake of the 1960 rat pack vehicle, George Clooney plays Danny Ocean, a career criminal assembling a crack team in order to pull off one of the biggest casino heists in history. Rounding out the cast are a perpetually hungry Brad Pitt, Matt Damon, Elliot Gould, Bernie Mac, Casey Affleck, Scott Caan, Qin Shaobo, Eddie Jemison, Carl Reiner, and Julia Roberts.

  1. State of Play – HBO | Cinemax  

This political thriller has an all-star cast, and is well worth the watch. Here, Affleck plays a young senator from Philadelphia, and his barely-there Pennsylvania accent is so good it’s scary.

  1. Gerry

Starring Casey Affleck and Matt Damon, Gerry is an allegory of sorts. As a part of Gus Van Sant’s death series, the story follows two men (both inexplicably named Gerry) who are lost in the desert after what was supposed to be a short hike. 

  1. Chasing Amy – Hulu | Tubi TV  

This Kevin Smith film is the classic tale of boy meets girl. Except, this girl, Alyssa (Joey Lauren Adams) has no interest in our boy, Holden (Affleck). Undeterred, Holden somehow manages to woo her, at least briefly. Damon also appears in a small role.

  1. True Grit  

This 2010 remake pairs Damon with screen vet Jeff Bridges and newcomer Hailee Steinfeld. Here Bridges reprises the role of Rooster Cogburn made famous by John Wayne. A young girl on a mission of justice after the death of her father enlists Rooster’s help, and along with him, Texas Ranger LaBeouf (Damon) accompanies her on her mission.

  1. Pearl Harbor – Amazon Prime | HBO

While this deeply romantic retelling of the attack on Pearl Harbor is nowhere near historically accurate, it is still a beauty to watch.

  1. We Bought A Zoo

This family-friendly film directed by James Cameron is loosely based on a true story and reunites Cameron and Patrick Fugit, who also worked together on Almost Famous. Here, Damon stars as a troubled father who buys a zoo in the hopes of making his kids happy and taking their minds of the loss of their mother.

  1. Boiler Room – Cinemax  

Boiler Room is the story of a corrupt group of stock brokers who are eager to make a buck no matter what the cost. The film stars Ben Affleck, Giovanni Ribisi, and Vin Deisel.  

  1. Project Greenlight – HBO

This 2001 documentary competition series chronicles Damon and Affleck’s search for a first-time director to greenlight. The show returned to HBO in 2015.

  1. Saving Private Ryan – Starz

One of the most beloved World War II films ever made, Saving Private Ryan is the story of a group of men who are sent to search for Private Ryan (Damon), a young soldier who’s two brothers have both perished in the fighting and is being sent home.

  1. The Company Men – Netflix  

This well-reviewed 2010 drama has an impressive cast, with Ben Affleck, Kevin Costner, Chris Cooper, Craig T. Nelson and Tommy Lee Jones. The Company Men is about a man who is let go during a company downsizing, and must figure out a new normal for himself and his family.

  1. The Bourne Identity – Cinemax

While there are a lot of Bourne movies, nothing really beats the original.

  1. Bending the Arc

Ben and Matt co-produced this gripping documentary about a group of medical professionals known as Partners in Health. These daring doctors and humanitarians are devoted to bringing life-saving care to people living in impoverished nations like Haiti, Rwanda and Peru. 

  1. Extract – Hulu | Tubi TV

This independent comedy stars Affleck in a supporting role as a scruffy bartender.

  1. The Legend of Bagger Vance – Hulu | Tubi TV | Showtime

Like the fairy godmother of sports dramas, Bagger Vance (played by Will Smith) comes into the life of golfer Rannulph Junuh (Matt Damon) just at the right moment and serves as the player’s caddy during an important tournament.  

  1. School Ties – Showtime | Epix  

School Ties the story of a talented football star (Brendan Fraser) who attempts to hide the fact that he is Jewish from his teammates and classmates (Chris O’Donnell & Matt Damon) while at preparatory school. When the truth comes out, he is shocked by the threatening actions of his so-called friends. (Affleck plays a minor role.)

  1. Hollywoodland – DirecTV Now | Starz

Hollywoodland is a fictional film that follows the investigation into the suicide death of the very real George Reeves. This stylish period film has an all-star cast and a delicious mystery at its center. 

  1. Jay and Silent Bob Strike Back – Hulu | Amazon Prime  

In Kevin Smith’s “Askewniverse” actors pop up here and there, often paying different roles, but all seemingly having grown up in the same town with the same “do you remember that time when…” stories. In Jay and Silent Bob Strike Back, Damon and Affleck actually play two characters each, Damon portrays himself as well as Will Hunting, his character from Good Will Hunting, and Affleck also portrays himself as well as Holden McNeil, his character from Chasing Amy.

  1. Forces of Nature – Amazon Prime | Tubi TV | Epix  

While it might not be Affleck’s best work, it’s kind of adorable and it’s got Sandra Bullock at her quirky best. There’s just something comforting about a light and easily watchable romance, and Forces of Nature has that in spades.

  1. The Adjustment Bureau

This sexy romantic thriller stars Matt Damon and Emily Blunt, a couple torn apart by evil forces that neither of them could have ever foreseen.

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