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Fun fact about me, I’m from the same hometown as Bill Murray – it’s a village called Wilmette, Illinois. Sometimes I sandwich that tidbit between a truth and a lie, but today I’m using it to introduce you, dear Cracked readers, to the world of Chicago’s North Shore, a swath of almost homogeneously white suburbs nestled along the coast of Lake Michigan and the setting of numerous comedy classics, including Ferris Buehler’s Day Off, Mean Girls, Home Alone, and my favorite, Caddyshack

TheCuriousGnome

This quite literally says it all.

Harold Ramis, Bill Murray, and Brian Doyle-Murray all spent their adolescent years lugging around golf bags for snooty suburbanites at a country club called Indian Hill in the town of Winnetka, Wilmette’s nicer northern next-door neighbor. 

Though Harold and the Murray brothers wouldn’t meet until many years later, their time at the members-only establishment inspired the three to create a raucous drug fest barely disguised as a movie which would become the defining film for the sport of golf, as well as the most memorable and entertaining takedown of condescending, classist, and capricious country club snobs. And the snobs at Indian Hill are still mad about it.

(We would have liked to have shown you an image of Indian Hill here, but none exists on the entire internet we could use. -Ed)

I recently sat down with a friend of mine over Zoom and asked him about the time he spent at Indian Hill. Danny, as we’ll (naturally) call him, worked as a caddy for five summers at the country club, spending most of that time in the actual caddyshack from Caddyshack. He was kind enough to share his experiences below:

I guess my first question is did people at Indian Hill ever talk about Caddyshack with you or was it a taboo subject?

Oh they brought it up on literally the first day. I’m not kidding, all the first year caddies would show up for orientation, and the first thing they told us was “Yes, this is the place from Caddyshack. Don’t bring it up again.” They told us directly to never mention it around members, because a lot of scenes in the movie are based on actual people whose families are still members, and they’re still upset about the portrayals. 

Did they say which scenes in particular were based on real people?

Yeah, but the only one I remember is that scene where the Italian guy is caddying for that really really old couple and he’s trying to help them find their balls, and the old lady chips it right into the pond and goes “wheee!” 

Orion Pictures

Yep, "wheee!”

I only remember it because on that first day when the caddymaster told us about it he actually said “wheee!” really loud, and that stuck with me. I hadn’t even seen the movie before, I just knew that “wheee!”

But you have seen Caddyshack right?

Oh yeah of course, but not until a few years later. I was too young when I first started. I think I was going into seventh grade. I definitely didn’t watch it until high school.

They let you caddy that young?

Yeah they let kids start caddying pretty early, most of us had never been on a golf course before we started there. I think eleven was the youngest you could be. Most of the real caddies were older though, like early to mid-twenties. Those were the professionals who actually got all the loops – that’s what it’s called when you caddy a round of golf, it’s a loop – the kids usually just sat around in the caddyshack all day.

Was the actual caddyshack anything like it was in the movie?

Not exactly, like I said it was a lot of younger kids so there wasn’t as much debauchery. Although the one thing they got right is how the caddies followed around the golfers taking bets on them, that definitely happened. There were certain holes where you could hide in the bushes and watch people play, and the high school kids especially would go there and bet on who was going to win the hole. The caddyshack itself wasn’t all that exciting, mostly we just sat around watching movies. Not Caddyshack of course, that one was strictly off-limits. There were a lot of other Bill Murray movies though, it wasn’t like a moratorium on him or anything, just not Caddyshack.

What were the members like at Indian Hill?

Probably the same as they are at any country club, I’d say about fifty percent of them were all snobby and mean but the rest of them were alright. The bad ones would always be looking for an excuse to yell at you, like any time they hit a bad shot it was because you were casting a shadow or holding the bag wrong or something like that. A lot like the Judge in the movie. They also called me “boy” a lot. Like half of the people I caddied for addressed me as “boy”. On the caddy uniform there are three places where your name is clearly printed, it’s on your hat, the front of your shirt, and the back of your shirt, but they still called you “boy”. I don’t think I really understood how messed up that was until I got older.

Did you have any positive experiences with members?

Oh sure, they weren’t all bad, like I said about half of them were exactly what you think of when you think of a-hole country club people, but the other half were good people, good tippers and all that. One guy in particular, he was in his eighties and he golfed eighteen holes every morning. He wore the same brown hat, and smoked the same cigars. They were these skinny licorice flavored cigars, kind of like cigarillos. He’d hand you a box of them before tee off and smoke one every couple holes or so. Every loop on the 15th hole he would offer you one, but you had to say no. That was part of our training, the caddymaster literally told us “when Mr. offers you a cigar, you say no thank you.” One time he was in the sand, and he let me take a chip shot, I got it onto the green on my first try and he gave me a hundred dollar bill. He was my favorite.

What about the president? Was he anything like Judge Smails?

I never met him, I have no idea. I doubt it, though. They actually treated us pretty well I think, the club that is. They were definitely embarrassed by the movie and made it a point to treat the caddies decently. Like free hot dogs, they made it a big presentational thing that all caddies were entitled to as many free hotdogs as they wanted. If you added up the cost of all the hotdogs I ate during my time there it’s probably more than all the money I made. I never knew the president though, I only heard about him. I remember one summer there was a story going around that his daughter had a black boyfriend, that was a big deal. I don’t know if you can include that.

Were there any other stories that stuck out? Any scandals?

I don’t know if it was really a scandal, but there was definitely one “bad boy” caddy. Long blond hair, surfer bro kind of guy. He was probably in his early twenties. He would get into trouble a lot, show up late, argue with the caddymaster, that sort of thing. He got away with it though because he had that sleazy kind of charm. I remember one time I was with him on a loop with some tennis moms, and they just ate him up. He was flirting and hamming it up, they just loved him. I don’t think they said a word to me the whole loop. On the back nine he lit up a cigarette right in front of them which just blew my mind. It was super against the rules for caddies to smoke on the course but he didn’t care. Then at the end of the loop he leaned over to me and whispered “if you ever need some weed, I can hook you up.” I was twelve.

Orion Pictures

“Do you take drugs, Danny? Because I’m selling.”

It’s been ten years since Danny last caddied at Indian Hill, and while a lot has changed in the world over that time, it seems like country clubs sure haven’t. It stands to reason that the fine folks at Indian Hill still have not forgiven their disgraced former caddies for turning their beloved luxury retreat into a mockery. 

While the actual filming of Caddyshack took place at a country club in Florida, most details in the script (minus of course some of the golf bag stereos) were taken directly from the experiences of Brian Doyle-Murray and his brother Bill at Indian Hill. They really did caddy to pay for their education. There really was a gambling addicted caddymaster who overcharged the kids on snacks. There was real snobbery, racism, classism, and disrespect towards the working kids who needed those demeaning jobs because it meant a possibility for a better life. 

Bill Murray said this about some of the members at Indian Hill: "The kids who were members of (the Indian Hill Club) were despicable; you couldn't believe the attitude they had. I mean, you were literally walking barefoot in a T-shirt and jeans, carrying some privileged person's sports toys on your back for five miles." Harold Ramis openly talked about how being a poor Jewish kid led to his exclusion at the club. 

It’s very possible that the mockery of Indian Hill in Caddyshack directly led to Danny’s experience being much more bearable. At his own speculation, it certainly appears that the club was ridiculed into creating a more positive environment for the employed youth of the North Shore. Sometimes it takes a massively successful cult classic to drag the bourgeoisie kicking and screaming towards progress.

As for the members of Indian Hill, for any remaining misgivings they have about Caddyshack, they will soon be able to put them to rest over some burgers and beers just a short drive away from their exclusive clubhouse. The Murray Bros. Caddyshack restaurant chain is set to open a new location in Wilmette by March, just a couple minutes away from Indian Hill. 

How’s that for closure?

Hack fraud Keegan Kelly has never set foot on the grounds of Indian Hill, but if you like his writing he has even worse stuff here.

For more ComedyNerd, be sure to check out:

The 5 Bill Murrays You Meet in Bill Murray Movies

The Onion': 5 Behind-The-Scenes Stories From America's Finest News Source 

Comedy Impressions That Changed Politics

Top image: HBO Max

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