When Does "Don't Tell Mom the Babysitter's Dead" (1991) Take Place?
"Don't Tell Mom the Babysitter's Dead" is a coming-of-age comedy film written by Neil Landau with Tara Ison that released June 7th, 1991. So when is "Don't Tell Mom the Babysitter's Dead" set?
It takes place in the year:
We know this because when the receptionist Carolyn and Head Inventory Clerk Bruce find Sue Ellen "Swell" Crandell's driver's license, it reads "EXPIRES 12-19-94" representing December 19th, 1994 AD near the top. Importantly, it says "12-19-73" representing December 19th, 1973 AD under "DATE OF BIRTH" and Bruce says, "She's only 17!" So it must be after 1973 AD and most likely before 1994 AD.

1990 AD
We know this because when the receptionist Carolyn and Head Inventory Clerk Bruce find Sue Ellen "Swell" Crandell's driver's license, it reads "EXPIRES 12-19-94" representing December 19th, 1994 AD near the top. Importantly, it says "12-19-73" representing December 19th, 1973 AD under "DATE OF BIRTH" and Bruce says, "She's only 17!" So it must be after 1973 AD and most likely before 1994 AD.
12.1,973 + 17 = 12.1,990.
Furthermore, the Crandell family car's license plate is only visible for an instant but it has a California car inspection certification expiration date sticker dated for "90" representing 1990 AD. So it is probably before the end of 1990 AD.
More specifically, a little more than halfway through the narrative when Vice President of Marketing Gus Brandon creepily buys flowers and concert tickets for Swell the date on the tickets clearly read "FRI 8:00 PM APR 6 1990".
Earlier, Swell attempts to use a fax machine for the first time the letter she's trying to fax is dated for a later date (some point from the 10th to the 19th, it's unclear) in "April". This doesn't make much sense on the surface but it is possible the letter is being faxed to have a copy weeks in advance and it is early April of 1990 AD. (As we shall see .)
HOWEVER, the top of the calendar in Senior Vice President of Operations Rose Lindsey's office can be seen and it's open to the "June/Juin" page. Since the story is specified to take place in the summertime this makes more sense than the April dates. It is therefore extremely likely it is June of 1990 AD and both April dates are production mistakes.
Later, at the end of the story Kenneth "Kenny" Crandell's friend says "Hey, you know school starts next week. Lazy days." and in the American public educational system, the school year starts in early September so it is almost certainly late August of 1990 AD at the end of the story.
Specifically, at the very beginning of the story Swell refers to her mother when she said to her friends, "I can't wait, I'm getting rid of her for 2 whole months, you guys." and at the end little Zach Crandell exclaims, "You weren't supposed to come home 'til next week!" So for only 7 weeks to pass it must be very late June at the start and late August at the climax.
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