I Just Found Out Ben Stiller And Robin Williams Helped Superman's Jimmy Olsen Actor Land His Prom Date, And They’re My Heroes For Making This Happen

Ben Stiller and Robin Williams in Night at the Museum.
(Image credit: Twentieth Century Fox)

In the pages of DC Comics, Jimmy Olsen is known as Superman’s pal and, so far, it seems that’ll also be the case in James Gunn’s upcoming film centered around the Big Blue Boy Scout. Skyler Gisondo is set to play Olsen in the highly anticipated 2025 movie schedule release, and he’s downright perfect for the role. Years ago, however, Gisondo received some assistance in real life from co-stars Robin Williams and Ben Stiller. I just learned that the actors helped Gisondo score a prom date, and this makes them heroes in my book.

Skyler Gisondo worked with the two beloved actors on Night at the Museum: Secret of the Tomb. Apparently, principal photography took place amid prom season and, while Gisondo’ buddies scooped up their dates, he did the same on set. To do so, he enlisted the help of his two co-stars, who helped him record a video for the young lady he hoped to escort to the prom. Ultimately, they produced one of the funniest prom proposals I’ve ever seen, and you can check it out below:

Skyler Gisondo's Prom Proposal (featuring Ben Stiller and Robin Williams) - YouTube Skyler Gisondo's Prom Proposal (featuring Ben Stiller and Robin Williams) - YouTube
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First off, I’m still trying to figure out how I’m only now becoming aware of this entire situation. I’m a fan of Robin Williams, and I’d usually catch wind of his antics one way or another. Nevertheless, I’m glad to have found it now, and I’m loving it. Both Williams and Ben Stiller bring a lot of charm and wit to the proceedings. I especially can’t help but make note of Williams’ killer improv skills, and I keep replaying him calling for dancers as well as Cirque du Soleil performers. The monkey with the rose is a sweet touch as well.

This is all definitely funny, but it’s also incredibly sweet, considering that the two veteran actors didn’t have to go to such great lengths to help their younger co-star. It’s been said that not all heroes wear capes, and I think that certainly rings true in this case. A gesture like this shouldn’t be overlooked, and Skyler Gisondo seemed to appreciate it. Gisondo spoke to THR about it around that time, and it sounds like he and his colleagues had a fun time putting it all together:

All morning, Robin was pitching more ideas. He was saying ‘Can I say this? Would it be appropriate to say this?’ You’re Robin Williams. You can say whatever you want! It turned into this three-minute, ridiculous thing. A prom-posal. I realized that was the most awesome three minutes of my life and I’ve accepted it will go downhill from there.

I’m not sure if Kal-El will help Jimmy Olsen find a date in the highly anticipated Superman, but I’m excited to see their dynamic nonetheless. Few castings feel as appropriate as Skyler Gisondo as Jimmy, given he not only looks the part but he also exudes the DC character’s boyish charm. He also gives “aw, shucks” vibes, which was on display when he talked about bringing his “best” to the role of Olsen.

Quite frankly, I’m a tad envious of Skyler Gisondo for putting together a successful prom-posal with two comedic titans like Robin Williams and Ben Stiller. I would hope that Gisondo holds onto this memory fondly, given that Williams passed away in 2014 at the age of 63. All in all, this is a humorously sweet reminder of a moment in time that not only signifies humor but also Williams’ propensity for caring for co-stars and Stiller’s sheer kindness as well. Those are certainly qualities that make a hero.

You can see a hero rise when Superman opens in theaters on July 11. In the meantime, read up on other upcoming superhero movies that are headed to the big screen.

Erik Swann
Senior Content Producer

Erik Swann is a Senior Content Producer at CinemaBlend. He began working with the publication in 2020 when he was hired as Weekend Editor. Today, he continues to write, edit and handle social media responsibilities over the weekend. On weekdays, he also writes TV and movie-related news and helps out with editing and social media as needed. He graduated from the University of Maryland, where he received a degree in Broadcast Journalism. After shifting into multi-platform journalism, he started working as a freelance writer and editor before joining CB. Covers superheroes, sci-fi, comedy, and almost anything else in film and TV. He eats more pizza than the Teenage Mutant Ninja Turtles.

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