I love that Adam is incapable of wearing anything but sweat pants and athletic shorts in his old age.
He’s also married to a super model. The man won life 19 times over.
Potentially one of the best to wear a Bears jersey, and Caleb Williams. Gotta love it
Can Adam help with his accuracy?!?
That pic is going down as a classic in 15 years
In talks for a movie together? One can hope…
Lmao just watched the Waterboy with my son for the first time yesterday. Perfect timing
My first thought is that he’s a Jets fan and the Bears have pretty much been the Jets of the NFC for the last half a century, so there for he is inherently a Bear fan.
Caleb and Rome were at his show last night at the UC. All went to ChicagoCut after for steaks.
Dang they really took this pic from a funny angle. Sandler is so much shorter than Caleb – kudos to Sandler team, ig?
You buttonhooked me. I didn’t know you were gonna buttonhook me.
![[Chicago Bears] Adam Sandler, what are you doing here?](https://www.rawchili.com/wp-content/uploads/2025/10/829afddl1iwf1-1080x1024.jpeg)
27 comments
This is pretty cool, especially with him wearing Caleb’s jersey
I thought he was a Jets fan?? o.o
What is that jersey
Do you think Caleb is a bigger fan of “The Waterboy” or “The Longest Yard”?
Apparently he was in town to perform some comedy.
is caleb eating pudding?
Bears signing Bobby Boucher?
Caleb and Rome were at Sandler’s show last night
Paul Crewe also wore number 18
https://preview.redd.it/eteefgof5iwf1.jpeg?width=904&format=pjpg&auto=webp&s=d7ac52928063267c71cdb708f36f2d5618ad924f
What are youuuuu doing here?!
That’s dope af
Sandys kind of mogging caleb here
Tacklin fuel
I love that Adam is incapable of wearing anything but sweat pants and athletic shorts in his old age.
He’s also married to a super model. The man won life 19 times over.
Potentially one of the best to wear a Bears jersey, and Caleb Williams. Gotta love it
Can Adam help with his accuracy?!?
That pic is going down as a classic in 15 years
In talks for a movie together? One can hope…
Lmao just watched the Waterboy with my son for the first time yesterday. Perfect timing
My first thought is that he’s a Jets fan and the Bears have pretty much been the Jets of the NFC for the last half a century, so there for he is inherently a Bear fan.
Caleb and Rome were at his show last night at the UC. All went to ChicagoCut after for steaks.
Dang they really took this pic from a funny angle. Sandler is so much shorter than Caleb – kudos to Sandler team, ig?
You buttonhooked me. I didn’t know you were gonna buttonhook me.
I don’t trust people that don’t love Adam Sandler
Officially my favorite picture of all time
Oh Caleb with the Air Yeeyzs
Tacklin’ Fuel.