During a Training Montage, there is something at the top of a flagpole, and a group of trainees are challenged to retrieve it in order to either pass basic training, or earn a promotion, or be the candidate selected from a number of applicants. Usually, whoever wins the challenge is someone who manages to figure out an unorthodox method, rather than someone who is simply physically fit enough to climb the pole. Often results in An Aesop about brains versus brawn, or whoever was giving the test telling the candidate that they were looking for someone with the ability to think creatively. Has nothing to do with Tongue on the Flagpole, even though someone usually does that as the result of a dare or challenge.
Anime and Manga
- In Brave Witches Rossmann challenges Hikari to fetch down a hat on top of an obelisk within a week if she wants to stay in Brave Witches, telling her to use her magic to Wall Crawl up the obelisk. She just barely makes it within the time limit when Rossmann instructs her to focus her magic onto one hand at a time instead of crawling up on all fours.
- Lampshaded in Quizzical: "All the books agree on this," said Scootaloo. "When you begin training you should have what looks like an impossible goal. When you figure out how to achieve your goal you've completed your training." Quizzical manages to retrieve the arrow by kicking the flagpole until the arrow falls out.
Films — Animated
- In Mulan, Shang fires an arrow into the top of a pole and challenges the recruits to retrieve it while carrying two heavy metal discs. None of the recruits are able to do so, until Mulan wins the challenge by taking the two heavy discs she was given and tangling them around the pole to counterbalance her climb.
Films — Live-Action
- Captain America: The First Avenger has Steve Rogers accepted from among the group of candidates because he knocked down the flagpole by removing the bolt that was holding the flagpole to the base (all of the other recruits just tried climbing the flagpole).
Live Action TV
- Cobra Kai featured a similar challenge. Kreese put a pot on top of a post about 6 feet high, and told his students to kick it off. Several students tried to kick the pot, but failed. Hawk kicked the post itself, causing the pot to fall off. When one of the students said he cheated, Kreese responded, "Unlike you, he did exactly what I told him to."
- The Harvey Danger song "Flagpole Sitta" is a reference to this trope.
- This is an integral part of a Real Life Wiccan May-Day celebration. After a tall maypole has been wound with colorful ribbons, guests will be challenged to climb to the top and retrieve a symbolic prize, often a rose, in their teeth.
- On November the 25th, 1783, to signal the end of The American Revolution, the British greased a flagpole that still had the Union Jack raised before they left New York City. A man named Jon Van Arsdale managed to climb up the top and replaced it with the American Flag.
- At the Naval Academy during Graduation Week, first year cadets must climb a tall monument. It's about six meters high, smooth, and at the top is a hat that's worn by freshmen. The cadets must replace the hat with one worn by senior cadets. To make it even more difficult and force the freshmen to get creative and use teamwork, upperclassmen grease the monument. Heavily.