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- Spider-Man: This first time Peter Parker proposed to Mary Jane (she wouldn't say yes this time) he did so by giving her a box of Cracker Jack, with the regular prize inside replaced by an engagement ring.
- When the Matrix version of Supergirl is dealing with becoming an Earth Angel, she discusses her situation with Clark over a box of Cracker Jack. He mentions that he and Pete Ross used to guess what the prize was, until x-ray vision took the fun out of it, but swears he hasn't x-rayed this box. After he's gone, she finds that the prize just happens to be a pendant shaped like an angel.
- Our Miss Brooks: In this film, the cinematic grand finale to the series of the same name, Mr. Boynton finds an engagement ring in the bottom of a box of Cracker Jack. However, before he can place the ring on Miss Brooks' finger, it's stolen by a female chimpanzee named Chiquita. No matter, now engaged, Mr. Boynton and Miss Brooks walk out of the zoo arm in arm.
- UHF has a scene where Stanley Spadowski notices — while on air — that the box of cereal he's hawking comes with a free toy. Saying, "Don't let your parents know you do this," he then disassembles the box to get at the toy, making a mess of the cereal.
- Earlier, George mentions that there's a neat prize inside each box of Mrs. Hockenberger's Butter Cookies, though we never learn or hear any more about it once we find out what box he's actually holding.
- In While You Were Sleeping, young Mary Callahan doesn't want her older brother, Jack, to eat her favorite breakfast cereal. When he protests that it's very special cereal, she complains that "last time [he] took the toy surprise."
- After the opening sequence of A Nightmare on Elm Street Part 2: Freddy's Revenge, Jesse's little sister digs through a box of cereal for the free prize, a set of small, plastic finger blades. The cereal, incidentally, is called "Fu Man Chews".
- The Dictator has a scene of Aladeen having cereal with one of his generals. As the general pours his cereal, the prize inside lands right in his bowl. Aladeen tells him to enjoy it, then immediately orders the general's execution.
- At the climax of Spaceballs, Yogurt tells Lone Starr that the Ring of the Schwartz - which he formerly claimed was enchanted - is cheap junk, that he got it from a box of Crackerjacks.
- In Charlie and the Chocolate Factory, the five Golden Tickets are placed inside candy bar wrappers. There are reports of rich people buying bulk orders of Wonka Bars and tearing through their wrappers in hopes of finding a ticket, presumably discarding the chocolate. In fact, this is how Veruca Salt's father got her a ticket — he bought up all the Wonka Bars he could and gave them to the workers in his nut factory to "shell" until the ticket was found.
- The short-lived television series The Wizard had an episode in which the title character had invented a little robotic beetle-like thing that was specifically designed to dig through boxes of cereal and retrieve the prize at the bottom.
- In Night Court, Judge Harry Stone ends up in the hospital because of abdominal pain. He thinks it could be his appendix, the head of a local Greasy Spoon thinks he poisoned Harry. When he takes a turn for the worse, the rest of the cast is worried sick. Turns out his box of Chocolate-Frosted Sugar Bombs had a toy whistle at the bottom and Harry ate it by accident.
Judge Stone: You know 'Zippy Bits,' that breakfast cereal that promises a free circus whistle in each box? Well I bought a box, polished off the whole thing. No whistle. I even called them. They said there was a whistle in every box. Guess they were right.
- One of the spoof ads on The Goodies was for Goodies Plastic Spacemen, which came in a cereal box with a free corn flake.
- In Scrubs, JD has a flashback where he had a box of cereal that ended up having, not one, but two secret spy decoder ring prizes, he gives one to Turk and they both claim it's the best day of their lives (even above Turk proposing to Carla).
- One episode of Psych begins with young Shawn trying to get the prize from a box of cereal, and then his dad shows him that the most efficient way to accomplish this is to just open the box from the bottom, teaching him about flipping perspectives. Shawn uses this to help solve the case and later get the prize when Gus attempted to claim the toy for himself by dividing the cereal a certain way.
- Gets called back to in a later episode when Shawn attempts to confess to Juliet for the first time. He mentions the kids who would flip the box to get it immediately or the ones who went through bowl after bowl until it happened on its own (along with a humorous third one of a kid who would eat anything, including the prize.)
- One incident in the Monk novel Mr. Monk on the Road has Monk figure out that a salmonella poisoning victim was murdered because the box with the contaminated cereal had a toy that wasn't in the boxes that were on the recall list.
- In a fake commercial from The Amanda Show, some kids eating the new cereal Meatloaf Crunch ("It's turning the milk chocolatey!"-"That ain't chocolate—that's gravy!") get lotion and a mousetrap in the box. Another fake commercial for Mammal O's Cereal featured LIVE ANIMALS in the bottom of the box!
- An All That sketch had a family taking free prizes out of all the grocery items, even the mayonnaise.
- The music video "I'm on a Boat" involves Andy Samberg discovering a coupon for a free boat trip for three in his cereal.
- Referenced in "Two Out of Three Ain't Bad" by Meat Loaf:
I know you're looking for a ruby in a mountain of rocksBut there ain't no Coup de VilleHiding at the bottom of a Cracker Jack box
- Happens frequently with Jason in FoxTrot.
- A Story Arc in Peanuts concerned getting one free marble in a box of Snicker-Snacks cereal. In one strip Charlie Brown told Shermy that the packing center made an error - there were 400 marbles and one Snicker-Snack.
- In one Sunday Strip, Garfield dived into a bag of cat food after Jon told him about the prizes at the bottom. Garfield surfaced with a whistle and Groucho Marx glasses.
- Cereal boxes with prizes in them have appeared more than once. One strip has Garfield throw the cereal all over the table (and Jon) to get the toy ring inside, another features a box that has no cereal in it, only a large toy robot, and a third one where Garfield accidentally ate not only the cereal but also the prize.
- In Do They Ever Grow Up?, a book of one-panel comics by Lynn Johnston, a boy, who has dumped three boxes of cereal on the floor, tells his disapproving mother, "I couldn't 'member which one had the free helicopter."
- Parodied in one The Far Side cartoon where a family of dinosaurs is having breakfast, the son digging though a box of cereal that advertises "Free Kid Inside!" on the box. His mother sternly tells him to eat his breakfast and look for it later.
- The first edition Ghostbusters RPG adventure module "Ghost Toasties" was about an ancient gem linking to the demon lord of sugar, Hagost, being given away as a prize at the bottom of the cereal box.
- At one point in The Secret of Monkey Island, Guybrush finds a box of his favorite breakfast cereal. The prize at the bottom turns out to be necessary to making progress.
- Layla in Eerie Cuties won a random prize with CD (see the next page) and one extra mood swing of her new good friend as a bonus in bonus. Yes, "she leads a charmed life".
- Fighter in 8-Bit Theater has mentioned that he has sometimes dug his arm into a cereal box in the urge to get the prize inside, resulting in quite a mess. Black Mage soon becomes horrified when he finds out that Fighter only washes his hands once a week.
- CollegeHumor: Why settle for one prize when you can get a cereal box made entirely of prizes? "All Prizes Cereal" has all the toys you crave without all that boring cereal. It's the best thing to happen to breakfast since marshmellows!
- An episode of Ren and Stimpy showed Stimpy's preferred method for getting at a Muddy Mudskipper cereal bowl caddy: He just gets a very big bowl and pours all of the cereal into it. After he claims his prize, he stuffs the cereal back into the box.
- The Simpsons had an early episode in which Bart tries to find a police badge in the bottom of his cereal. It turns out Homer got to it first.
- Another episode features a box of Krusty-O's brand cereal that comes with a free jagged metal O at the bottom. Bart accidentally eats it, and wins a court settlement from the company, which he then spends on something for Lisa, because she was the only one who believed he was sick. He plans to get another settlement from the new Krusty-O's prize - flesh eating bacteria.
- In the Phineas and Ferb episode where they make working X-ray specs, the boys use them to look into cereal boxes to figure out which boxes contain the good prizes.
- At the start of the SpongeBob SquarePants episode "Shanghaied", SpongeBob is shaking his cereal box to find the toy inside. Just then, a giant anchor crashes into his house, leading to the line: "Squidward! The sky had a baby in my cereal box!"
- Also, in the episode "Waiting", SpongeBob misreads a "Free Prize Inside" message by ignoring the small print advertising a "free prize offer inside". After sending in the offer, the titular wait is SpongeBob's wait at the mail box for the prize to arrive.
- Taz-Mania once had a bit where Taz went to insane lengths to get the prize from a box of cereal...which turned out to be one of those baking-powder propelled submarines.
- An episode of Cow and Chicken is about Chicken finding a credit card in a cereal box. Also, in the episode where he gets insomnia after eating coffee-flavoured cereals, he finds a pair of underpants for prize.
- An episode of The Angry Beavers featured Norb and Dag competing over a variant: the boxtop prizes. Dag would reach in and grab the prize at the bottom, but Norb would clip boxtops and mail them back (and receive a much better prize in return).
- In an episode of The Fairly OddParents, this trope is exploited by a race of super-cute aliens, who use their charm to take over other planets by making the inhabitants of said planets want to buy more Giggle-Pie "Merchandise".
- In Family Guy, Jeremy Irons is adamant to point out there is no prize at the bottom of his cereal.
- In an episode of Timothy Goes to School, Nora decided to forego her normal breakfast cereal in favor of something called "Weeds and Seeds" so that she could get the prize of emerald slippers at the bottom as a birthday present for Yoko. And she was such a good little girl that she actually ate the stuff, only to find that to her disappointment, there was only one slipper, and it was some dinky little thing. Her mother suggested making a necklace out of it and she did, but thought her gift was lame and didn't want to give it to Yoko at first. When she finally did, Yoko was delighted, as the slipper was the mate to one that she already had.
- In "No Tradebacks!" in the fifth season of Caillou, Caillou gets a small toy shovel as a prize in a cereal box, but is upset because it's not the stickers that he wanted— ones like those that Rosie got when it was her turn to get the free prize. He trades it with a friend Jay for a set of the stickers and they agree to "no tradebacks," but then Caillou is upset that he traded it away when he sees that Jay attached it to his dump-truck, this being a feature of the shovel. He cajoles Jay so much that Jay finally agrees to a tradeback anyway, but when Caillou sees how upset Jay gets, he finally honours the original agreement.
- In "Franklin's Fossil" on Franklin, the title character and his best friend Bear have been collecting a series of a colored spinning tops that they're using as models of the solar system. The last one that they need is a purple one that's supposed to represent Pluto (this being back when it was still a planet) and when Mr. Mole sees them playing with them, he mentions having found the purple one in his cereal box. Later, when Mr. Mole gives it to them, Bear is thrilled that they can finally start eating some different cereal.
- The episode "Tag Yer Ed" from Ed, Edd 'n' Eddy begins with the Eds obtaining a box of Chunky Puffs, which Eddy points out has a prize inside (a giant marshmallow). Ed, being Ed, reads the "Low in Fat" label and assumes the fat is the prize.
- The Johnny Test episode "Johnny-O's" is centered around this. Johnny is sick about all the lame laser guns that come with cereal boxes, so he decides to create his own cereal—with a working laser gun as a prize inside. It comes back to bite him when Porkbelly goes crazy with the guns.
So what's the free prize at the bottom here? A Stinger? Aww... I already got one of those :(