If You Liked The Rip, These 10 Matt Damon and Ben Affleck Movies Are Must-Watches

If You Liked The Rip, These 10 Matt Damon and Ben Affleck Movies Are Must-Watches

Matt Damon and Ben Affleck have been Hollywood’s most iconic duo for decades, sharing a friendship that started in childhood and evolved into one of the most successful creative partnerships in film history.

If you enjoyed The Rip and want more of their dynamic collaboration, you’re in for a treat.

From Oscar-winning dramas to offbeat comedies, these ten films showcase their range, chemistry, and undeniable talent both in front of and behind the camera.

1. Good Will Hunting (1997)

When two childhood friends from Boston wrote a screenplay about genius and loyalty, they changed cinema forever.

Good Will Hunting earned Matt Damon and Ben Affleck an Oscar for Best Original Screenplay, launching them from unknowns to Hollywood royalty overnight.

Damon plays Will, a troubled janitor at MIT who happens to be a mathematical genius.

Affleck plays his best friend Chuckie, whose unwavering support and tough love push Will toward a better life.

Their real-life friendship bleeds into every scene, making the bond between their characters feel authentic and deeply moving.

Robin Williams delivers a legendary performance as Will’s therapist, adding emotional weight to an already powerful story about identity, class, and choosing your own path.

2. The Last Duel (2021)

Medieval France comes alive in brutal, unflinching detail in Ridley Scott’s historical drama co-written by Damon and Affleck.

Based on a true story, the film explores a violent conflict told through three radically different perspectives.

Damon plays Jean de Carrouges, a knight seeking justice through trial by combat, while Affleck steals scenes as the flamboyant Count Pierre d’Alençon.

Their screenplay, co-written with Nicole Holofcener, examines truth, power, and how stories change depending on who’s telling them.

The film’s structure keeps you questioning everything you’ve seen.

Each retelling reveals new truths and biases, building toward a climactic duel that’s as emotionally devastating as it is physically intense.

It’s a mature, thought-provoking work that showcases their growth as storytellers.

3. Dogma (1999)

Ever wonder what would happen if two fallen angels found a loophole to sneak back into Heaven?

Kevin Smith’s wildly imaginative comedy answers that question with Matt Damon and Ben Affleck playing rogue angels Loki and Bartleby.

The duo brings charismatic energy to roles that mix humor with existential stakes.

Damon’s Loki is vengeful and unhinged, while Affleck’s Bartleby is more contemplative and conflicted.

Their chemistry makes even the most absurd theological debates entertaining.

Packed with Smith’s signature irreverent humor and featuring an ensemble cast including Linda Fiorentino, Chris Rock, and Alanis Morissette as God, Dogma became a cult classic that still sparks debates about faith, redemption, and whether wings are overrated.

4. Chasing Amy (1997)

Kevin Smith’s romantic comedy-drama explores love, identity, and insecurity through Ben Affleck’s vulnerable performance as Holden McNeil, a comic book artist who falls for a woman with a complicated past.

Matt Damon appears in a memorable cameo that perfectly captures Smith’s sharp, conversational style.

Affleck carries the film with surprising emotional depth, showing range beyond his action hero persona.

His character’s journey through jealousy and acceptance feels painfully real, even when wrapped in Smith’s witty dialogue and pop culture references.

Damon’s brief appearance as an executive adds another layer to Smith’s interconnected Askewniverse.

The film tackles themes that were bold for 1997 and remain relevant today, proving that sometimes the best love stories are the messy, imperfect ones that challenge us to grow.

5. Jay and Silent Bob Strike Back (2001)

Chaos reigns supreme when Kevin Smith’s stoner duo hit the road to Hollywood in this meta-comedy packed with celebrity cameos and inside jokes.

Matt Damon and Ben Affleck show up as exaggerated versions of themselves, poking fun at their Good Will Hunting success.

Their scene together on the Miramax lot is comedy gold, riffing on Hollywood egos and the absurdity of fame.

Smith’s script lets them playfully mock their own images while celebrating the friendship that made them famous.

The entire film is a love letter to Smith’s devoted fans, rewarding anyone who followed his interconnected universe from the beginning.

Damon and Affleck’s willingness to laugh at themselves adds another layer of charm to an already hilarious, profanity-laced road trip through pop culture.

6. Jay and Silent Bob Reboot (2019)

Nearly two decades later, Kevin Smith brought his beloved characters back for a nostalgia-fueled adventure that once again features Matt Damon and Ben Affleck.

The reboot lovingly mocks modern Hollywood while celebrating the friendships and fandom that sustained Smith’s career.

Damon and Affleck’s return feels like a reunion with old friends, their brief appearances reminding fans why their partnership became legendary.

Smith’s script balances genuine heart with self-aware comedy, acknowledging how much has changed while honoring what made the original films special.

The film works as both a standalone comedy and a culmination of Smith’s interconnected universe.

For fans who grew up with these characters, seeing Damon and Affleck back in the fold is a warm reminder of where it all began.

7. School Ties (1992)

Before they were stars, Matt Damon and Ben Affleck appeared together in this powerful prep school drama about prejudice and privilege.

Set in the 1950s, the film follows a working-class Jewish student on a football scholarship who faces antisemitism when his background is revealed.

Both actors play supporting roles as students at the elite academy, early glimpses of the talent that would soon make them household names.

The ensemble cast also includes Chris O’Donnell and Brendan Fraser, making it a fascinating time capsule of ’90s rising stars.

The film tackles serious themes of identity, belonging, and moral courage with intelligence and restraint.

Watching Damon and Affleck in these early roles, you can already sense the charisma and screen presence that would define their careers just a few years later.

8. Glory Daze (1995)

On the cusp of their breakthrough, Ben Affleck starred in this indie comedy-drama about college friends facing the uncertain future after graduation.

Matt Damon makes a very early cameo appearance, another glimpse of their pre-fame years working together.

The film captures that specific anxiety of leaving college and entering adulthood, when the safety net disappears and real life begins.

Affleck plays one of several friends struggling to let go of their carefree days and embrace responsibility.

While not as polished as their later work, Glory Daze offers a raw, authentic look at a pivotal life transition.

Watching it now, knowing what came next for both actors, adds poignancy to this snapshot of two friends on the edge of everything they’d dreamed about.

9. Air (2023)

Behind every iconic sneaker is a story, and Air tells the fascinating tale of how Nike bet everything on a rookie named Michael Jordan.

Ben Affleck directs and plays Nike founder Phil Knight, while Matt Damon stars as Sonny Vaccaro, the marketing executive who saw Jordan’s potential before anyone else.

The film captures the underdog spirit of 1980s Nike competing against industry giants.

Damon brings charm and desperation to Sonny’s obsessive pursuit of the impossible deal.

Affleck’s direction keeps the corporate drama surprisingly tense and emotionally resonant.

What could have been a boring business story becomes a celebration of vision, risk-taking, and believing in something bigger.

The chemistry between Damon and Affleck, now as star and director, proves their partnership remains as strong as ever.

10. Jersey Girl (2004)

Kevin Smith shifts gears into tender territory with Jersey Girl, a heartfelt drama that leans on everyday mistakes and second chances.

Ben Affleck anchors the story as a widowed father stumbling toward purpose, guided by small kindnesses and awkward truths.

You will feel the tug between ambition and love in scenes that breathe.

Matt Damon drops in for a quick, memorable cameo as a PR executive, adding wit and a wink without stealing focus.

The film’s New Jersey warmth wraps around moments of grief and goofy hope.

If The Rip moved you, this soft landing of redemption will resonate.