Movies Filmed in Chicago: Adventures in Babysitting


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About a month ago, I was downtown and needed to meet my dad at the Prudential building to grab a ride home. I can’t say my dad was shocked when I called him three times asking for directions because if directionally challenged people had a poster child it would be me.  The conversation went like this:

    Dad: Okay, what direction are you going?
    Me: Oh, please. Um, I just passed a Walgreens and a man playing the saxophone?
    Dad:  Ok, do you see a building with a blue, giant, very visible sign that says Prudential?
    Me:  No, but I can sense your sarcasm, or your frustration. Or you’re making fun of me…
    Dad:  Do you see the Adventures in Babysitting building?
    Me:  Of course.
    Dad:  Walk towards it and I’ll meet you.
    Me: (distracted) Man, they just don’t make them like they use to.
    Dad: What? The buildings?
    Me: No, the movies.

I think it’s safe to say that not many people know the exact name of the “diamond building*” or the “Adventures in Babysitting Building**.”  I doubt Sara Anderson even knew the name and she was the one scaling down the building in attempts to get away from the mean Mr. Bleak, who just wanted the Playboy Magazine the kids stole from him while they were being held captive after they discovered his chop shop where he stole cars and sold them for parts. (Like I said, they don’t make ‘em like they use to). 

I was shocked when I found out the majority of the movie, with the exception of certain scenes, was actually filmed in Toronto rather than Chicago. The babysitter, Chris Parker, and the kids she babysits for, Sara and Brad Anderson, and Daryl Coopersmith are said to live in Oak Park, Illinois yet the cast and crew never actually set foot in the suburb. They did however get to experience that great feeling many of us have had on the Dan Ryan of racing towards the perfectly lit Chicago skyline at night. Both the breakdown scene in the beginning and the race home at the end take place on the famous Chicago expressway.

Oh, and don’t forget about Brenda. They wouldn’t even be on this great adventure if it wasn’t for Brenda, who ran away from home and is stranded at the old bus station on 20 E. Randolph Street (which is now a parking garage). And last but not least, the famous scenes in the Smurfit-Stone Building*** where Sara nearly plummets to her death, Chris and the gang almost get caught by the angry chop shop guys, while Mr. and Mrs. Anderson are coincidentally attending a party in the same building.

Though the numbers of scenes actually filmed in Chicago are limited, the references to the Windy City are not. Chris, Brad, and Daryl go to “Hemingway High” which is written on the Letterman’s jacket Brad wears during the entire movie. This high school doesn’t exist, but Ernest Hemmingway was in fact a native of Oak Park. In an attempt to get away from the angry mobsters, the kids run into a bar where they are forced to pay tribute to the Chicago Blues by singing an impromptu blues song. After their rendition of “Babysitting Blues,” Brad and Daryl stumble their way into a party at the University of Chicago where The Bears and the University are both referenced.

One of my all-time favorite scenes in the movie takes place on the “L” when two rival gangs, decked out in sweatbands, black leather jackets, and red leather vests, threaten to kill one another. They reference Jefferson and Jackson before whipping out their knives.

I can’t say that I’ve ever had to drive downtown, escape angry mobsters tailing me, survive a gang fight, pick up my friend from the train station, get home before the parents do and most importantly, have the kids in bed before bedtime. But I can relate to the moral of this movie. Chris Parker said it well after defeating the Lords of Hell on the L — “Don’t f$#! with the babysitter.”

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 *Okay name for the building.

**Best name for the building.

***Worst name for the building.

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