10 Powerful Good Will Hunting Moments

10 Powerful Good Will Hunting Moments

Legendary.  This is a label I do not hand out often but Good Will Hunting is more than deserving of legendary status.  It’s one of my favorite movies of all time.  A sentiment shared by millions who adore the amazing tale of a young genius from Boston.

10. Carlton Fisk

Matt Damon & Ben Affleck’s remarkable Oscar winning screenplay is full of wonderful character moments.  #10 on my list is a perfect example of the depth and richness of their scripting precision.

In a single speech, they are able to convey an immense amount of information on love, relationships and regret.  In addition, they also weave in a historic Red Sox moment that deepens the connection of two broken men.

You’ll hear this a lot as we countdown to #1 but the performances in Good Will Hunting are absolutely incredible and this scene is one of the best.

9. The NSA

Sticking with the strengths of the screenplay, this is another example of how powerful a well written screenplay can be.  It’s a simple monologue at first glance but every viewing reveals more nuance that’s elevated by leaving the camera on Will and letting him speak his mind.

The transition to Will & Sean’s conversation about Soul Mates is phenomenal.

8. How Do You Like Them Apples?

Speaking of monologues, is there anything better than seeing Will make this arrogant jerk look like a complete idiot?  Moments like these in movies are rare as the unlikable character tends to come out on top in many exchanges.  Especially in the first act.

Thankfully, our man Will is wicked smart.

(Jerk store!  That’s the line!…  Sorry, I can never resist a Seinfeld reference)

7. What Do You Want To Do?

I mentioned the ‘Soul Mate’ conversation earlier.  It may be the same scene but it completely deserves it’s own spot on my list.  Sean’s intelligent enough to know he has to break Will down in order to build up his confidence anew.  It’s a destructive scene that simultaneously shows Sean’s dedication and Will’s willingness to resort to anger.

I’m no good at chess but these two…

Honorable mention: Super Philosphy

6. Winning Lottery Ticket

More brilliant monologues.  This time Ben Affleck gets his moment and what a moment it was.

XTRA | Good Will Hunting: An Oral History | Boston Magazine

5. Einstein & Field’s Medals

Sean Maguire vs Gerald Lambeau round one.  A fantastic battle of intellect.  Amazing how they managed to fold Albert Einstein and Ted Kaczynski in the same coherent scene.

4. Math On Fire

Professor Lambeau’s passion is on full display the second Will lights a few pages on fire.  A final incredibly effective line of dialogue sums up the entire movie in one touching moment.

3. I Don’t Love You

Easily the most gut wrenching moment of the film where Will is finally honest with Skylar about his past.  The first time you see it, it’s impossible not to assume he will tell her he loves her.  Minnie Driver’s performance is incredibly poignant showing the full extent of her heart break.

2. Michaelangelo, Shakespeare, Love & War

This is it.  The scene (I fell) won Robin Williams his Oscar for best supporting actor.  There are many monologues in Good Will Hunting but this one dives into the depths of both Sean & Will in extremely personal ways.  Unreal.

1. It’s Not Your Fault

I like to think that everyone who gives Good Will Hunting a chance will enjoy it.  But it’s THIS scene that makes people fall in love with the story.  Everything about this scene is perfect including the satisfying smile on Sean’s face when will finally let’s it all go.


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