The SNL Sketch That Made Adam Sandler Laugh The Most On Air (And, Of Course, It Involves Chris Farley)

Adam Sandler is famous for making people laugh, especially during his time on Saturday Night Live. He appreciates a good joke himself, and while many have tried, Chris Farley – his fellow SNL star – was particularly successful at cracking him up. Sandler recently shared that one sketch with Farley stands out as the funniest he experienced live on the show.

Adam Sandler and Timothée Chalamet recently chatted with each other for an awards season interview, and their conversation was filmed by Vanity Fair and posted on YouTube. During the interview, they watched a clip from a 1993 sketch on Saturday Night Live – “The Herlihy Boy House-Sitting Service.” Sandler then shared a story about a friend who helped him with the sketch.

The character I played on the show was called The Herlihy Boy, and I actually wrote that sketch. My friend, Tim Herlihy, wrote a lot of my early movies – things like Billy Madison and Happy Gilmore. We were college roommates, so I’ve known him for a long time.

The popular YouTube sketch, with over two million views, features Adam Sandler as Herlihy Boy. Presented like a fake advertisement, the sketch shows Herlihy attempting to persuade homeowners to allow him to do things like water their plants and sleep in their beds while they’re on vacation. He’s assisted by Mr. O’Malley, a comically enthusiastic character brilliantly played by Chris Farley. Sandler recently shared that the entire sketch was put together very quickly and with little advance planning.

I wrote that sketch one late night when I wasn’t scheduled to be on the show. Lorne Michaels asked if I had any ideas for a sketch, and I suddenly had a chance to write something new. I immediately included Chris Farley in it, because I, like everyone, was a huge fan. I think I laughed more at him during that sketch than at anyone else – anything he said just cracked me up.

Fans watching the sketch might notice Adam Sandler struggling to keep a straight face, and it turns out Chris Farley was deliberately trying to get that reaction. Sandler later explained Farley’s specific tactic for making him laugh.

Before every performance, Chris Farley had this playful ritual with me. He’d yell ‘Adsy!’ – that was his nickname for me – and declare he was going to get me. I’d immediately start bracing myself, knowing he’d try everything to make me crack up. He lived for that reaction! If he could make me break, he considered it a victory, proof he could out-funny anyone. Honestly, the guy was the funniest person I’ve ever known. When he walked into a room full of comedians, there was just this instant acknowledgement – everyone knew he was the best. It wasn’t even a debate; we all agreed Farley was unbelievably hilarious.

It’s no surprise Adam Sandler couldn’t keep a straight face – Chris Farley was incredibly funny. He was a master of making people laugh, and the “Herlihy Boy” sketch is a perfect example. Even now, just imagining Mr. O’Malley’s over-the-top plea is enough to make me smile. You can watch the hilarious scene below:

It’s hard not to feel moved when you watch that sketch – it really brings home the loss of a truly gifted performer. Chris Farley struggled with addiction and tragically died of an overdose in 1997. But he’s definitely not forgotten; people still talk about him fondly, and his work continues to be highly influential.

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Over the years, Adam Sandler has often spoken fondly of his friend Chris Farley, and is well-known for his tribute song dedicated to him. It’s been a long time since they worked together, but Sandler still lovingly remembers Farley and his comedy. If you’d like to revisit Farley’s work, you can stream classic episodes of Saturday Night Live with a Peacock subscription.

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2025-12-03 20:39