Spider-Man may be heading into Brand New Day, but some moments are impossible to forget.

Over three films—Captain America: Civil War, Avengers: Infinity War, and Avengers: Endgame—Anthony and Joe Russo helped shape Tom Holland's Peter Parker from an eager Queens teenager into one of the MCU's emotional centerpieces. Along the way, they delivered some of Spider-Man's funniest, biggest, and most heartbreaking scenes.

Before Peter begins his next chapter, we're looking back at ten Russo Brothers moments that still stick with fans years later.

10. "I'm Peter, by the way."

🎬 Film: Captain America: Civil War
⏱️ Rewatch Moment: ~1:43:00

In the middle of the biggest superhero showdown Marvel had ever put on screen, Peter Parker does the most Peter Parker thing imaginable—he introduces himself. It lasts only a few seconds, but it instantly separates him from every other hero in the MCU. The suit may have been new, but the heart of Spider-Man was already there.

9. "Underoos!"

🎬 Film: Captain America: Civil War
⏱️ Rewatch Moment: ~1:41:00

One word. One shield. One entrance that changed the MCU forever.

Tony Stark's call sends Spider-Man swinging into the airport battle, announcing a new generation of heroes with one of Marvel's most iconic introductions.

7. "You ever see that really old movie... Empire Strikes Back?"

🎬 Film: Captain America: Civil War
⏱️ Rewatch Moment: ~1:48:00

Leave it to Peter Parker to save the universe with a movie reference.

His idea to immobilize Ebony Maw using The Empire Strikes Back isn't just one of the funniest moments in Infinity War—it's also the plan that works. Classic Spider-Man: nerd first, superhero second.

6. The Iron Spider

🎬 Film: Avengers: Infinity War
⏱️ Rewatch Moment: ~0:24:00

The Iron Spider suit isn't just an upgrade—it's a passing of the torch. For the first time, Tony Stark stops trying to protect Peter from the fight and instead gives him everything he'll need to survive it.

5. "Mr. Stark... I don't feel so good."

🎬 Film: Avengers: Infinity War
⏱️ Rewatch Moment: ~2:17:00

There are plenty of unforgettable endings in Marvel history.

This might be the one that broke audiences the most.

Peter doesn't disappear instantly like everyone else. He feels it happening. He fights it. He reaches for Tony. Years later, it's still impossible to watch without holding your breath.

4. Through the Portals

🎬 Film: Avengers: Endgame
⏱️ Rewatch Moment: ~2:18:00

Five years after disappearing, Peter Parker swings back into the fight like he never left.

It's one of those movie moments that audiences don't just watch—they celebrate.

3. "Hey, Mr. Stark."

🎬 Film: Avengers: Endgame
⏱️ Rewatch Moment: ~2:20:00

Peter talks a mile a minute.

Tony doesn't say a word.

He simply hugs him.

After everything they'd been through, it was exactly the reunion both characters—and the audience—needed.

2. "Activate Instant Kill."

🎬 Film: Avengers: Endgame
⏱️ Rewatch Moment: ~2:24:00

A feature Peter once wanted nothing to do with becomes the only way forward.

The callback lands because Peter has changed. The kid who hesitated in Homecoming now understands exactly what's at stake.

1. The Final Battle

🎬 Film: Avengers: Endgame
⏱️ Rewatch Moment: ~2:18:00–2:45:00

Peter Parker entered the MCU trying to prove he belonged.

By the end of Endgame, there was no question.

Standing shoulder to shoulder with every Avenger in one of the biggest battles in cinematic history, Spider-Man wasn't the future anymore.

He was already one of them.

It's difficult to imagine the MCU without Tom Holland. From his unforgettable entrance in Captain America: Civil War to some of Marvel's most emotional moments in Infinity War and Endgame, Peter Parker has become one of the franchise's defining characters. It almost didn't happen that way.

In an early interview reflecting on Captain America: Civil War, Joe Russo revealed that casting Holland wasn't a simple decision—it became a months-long campaign.

"We talked with Feige at Marvel about Holland and he got excited and then we went to Sony... And they were like, 'Let's think about it for a minute.' We could tell we were meeting resistance from Sony. So we brought him back, brought him back, brought him back, and we were relentless in our pursuit of jamming him down the throat of the studio who owns this IP." — Joe Russo

Anthony Russo explained that Sony's hesitation wasn't about Tom's talent. It was about redefining one of the world's biggest superheroes.

"It was the first time Spider-Man had ever been cast as an actual teenager. Which was very important to us." — Anthony Russo

More Than One Movie

The Russo Brothers' belief in Tom Holland didn't end with Spider-Man.

After introducing him to the MCU in Captain America: Civil War and directing him through Avengers: Infinity War and Avengers: Endgame, Anthony and Joe cast Holland as the lead in Cherry, AGBO's first feature film. It was a dramatically different role—one that showcased a side of Holland audiences hadn't seen before—and reflected the trust that had grown between actor and filmmakers over years of collaboration.

That relationship continues beyond the screen. In 2024, Tom and his brother, Harry Holland, joined AGBO and Joe Russo in Scotland for the Sands International Film Festival, supporting AGBO's partnership with the festival and celebrating storytelling alongside filmmakers and audiences from around the world.

Some collaborations last for a single project. Others become creative partnerships that continue to grow. Tom Holland's relationship with Anthony and Joe Russo has become one of those rare Hollywood collaborations—one built on mutual trust, shared ambition, and a willingness to keep telling stories together.

As Peter Parker begins a Brand New Day, it's hard to imagine the Marvel Cinematic Universe without Tom Holland. And looking back, it's just as hard to imagine his journey without the Russo Brothers—filmmakers who saw something special long before the rest of the world did. Some casting decisions shape a movie. This one helped shape an era.

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