A very common prank among school-age children is to pilfer underpants from someone and hang it from a flagpole like a flag. The underwear will often be Goofy Print Underwear. Instances where the wearer is not removed from the underpants first count as a Wedgie.
Compare Comedic Underwear Exposure, which is something similar on a person. Not to be confused with Flag Bikini, which is swimwear or underwear in the color and pattern of a national flag. See also Panty Thief, who steals and keeps underwear for (usually) perverted reasons.
- In Jimmy Neutron: Boy Genius, after all of the adults have been kidnapped by the Yolkians, the kids have fun for the entire day, including hanging up a pair of briefs on the flagpole and saluting it.
- Used by the Arabian army in Follow That Camel to mock the French Foreign Legion's morning march, when a pair of bloomers are attached to the flagpole; the Arabian soldiers and their leader don't even attempt to hide themselves, and conspicuously shriek with laughter on the nearby balcony as the Legion's staff threaten to punish their soldiers.
- RocketMan (1997): While on their historic mission on Mars, Fred Randell loses the American flag in one of his many blunders throughout the film. He valiantly offers a replacement with "... a better flag, a high-flying flag!". Cue national live broadcast of Fred hanging his American flag boxer shorts onto the pole. The American president was not amused. In The Stinger, a Martian is shown walking off wearing said underwear-flag.
- Herrod Sayle, the villain of the Alex Rider novel Stormbreaker, was subjected to severe bullying after he moved from Egypt to England at age 7, which included his underpants being run up the flagpole.
- The Berenstain Bears: The Big Chapter Book At Camp Crush has someone pulling a lot of pranks at Camp Grizzmeyer, the last of which is a variant on this — instead of underwear flying at the top of the flagpole, it's Mr. Grizzmeyer's striped pajama bottoms. It turns out to have been done by the Too-Tall Gang, who were bored at home since most of their classmates were off at the camp for the summer.
- The novel Who Ran My Underwear Up the Flagpole?, as the title suggests, has this as a major occurrence.
- A related example from Dave Barry when he visited his son's dorm room:
I'm not complaining about my son's housekeeping. He is Martha Stewart compared with the student who occupied his bedroom last year. According to true campus legend, when this student moved out, his laundry was so far beyond human control that he simply abandoned it. As a kind of tribute, his roommates took a pair of his briefs outside, climbed a lamppost and stretched the briefs over the lamp. They remain there today, a monument to the courage and dedication it takes to put underpants on a lamppost.
- Double Dare (1986):
- The 1992 Family Double Dare season had one on the raft used to cross New Lake Double Dare.
- Another one appears in the 2018 reboot obstacle One Nation Underwear in which a contestant must pull boxer shorts up a flagpole to bring down the flag that they need to pass to their partner.
- M*A*S*H: In the episode "Cowboy", the hole marker for the golf course Hawkeye and Trapper laid out is a brassiere.
- In the series Salute Your Shorts, this trope happens in both the opening title sequences and the first episode's teaser, where Budnick and Donkeylips take the camp flag down and put up a pair of boxer shorts in its place. Three pairs that are different from those in Season 1 are used in Season 2's title sequence. Despite the different shots used each time, the Season 1 title sequence boxers match Michael's, so it's implied to be his in both instances. The instance in the aforementioned teaser prompts a Title Drop from Sponge in-episode.
- The Two Ronnies: In the Piggy / Charley serial "Death Can Be Fatal", the protagonists' bungling results in the hotel's flag getting swapped for a pair of knickers, which, to the pompous under-manager's horror, get run up the flagpole before anyone realizes.
- The first world of Plok has the title character trying to hoist a flag onto the pole at the end of each level, only to find that the flag's been replaced by something else: in the very first level, he hoists up a pair of boxer shorts.
- Red vs. Blue: Part of the Blues and Reds' backstory involves the Blues misplacing their flag and losing the map showing where it was hidden, with Loco making a replacement flag out of a wooden pole and a pair of underpants. Carolina is not pleased by the situation when she arrives at Desert Gulch for a sparring match with Tex. Said underwear flag accidentally becomes Biff's murder weapon after Carolina deflects it towards him and impales him to the wall when Tex throws it at her, with Tex violently pulling it out of his abdomen and causing Biff to bleed out and die.
- The Onion: "Deceased Nerd's Underpants Flown at Half-Mast."
- In the Arthur episode "Arthur Goes to Camp"; the girls pull this prank on the boys.
- In an episode of Babar, Zephyr the monkey pulls up Cornelius's underpants on a flagpole in place of the royal flag as a prank.
- Doug gets his first camp out as a Bluff Scout. Roger offers to take care of him, but just spends the time finding ways to torment him, including flying his briefs from the flagpole.
- The Ed, Edd n Eddy episode "Home-Cooked Eds" had the Kankers spending their summer holiday by parking their trailer in Eddy's front yard. Later, they manage to get inside his house and rummage through Eddy's room, where Marie finds a pair of leopard skin underpants, much to Eddy's embarrassment. Afterwards, they decide to hang it up as a sign of taking over Eddy's home for the rest of their vacation.
- A variation on The Fairly OddParents! episode "Pipe Down!". After Timmy wishes for no sound, Timmy raises Francis the Bully on a flagpole by stringing his underpants and having a hungry dog help raise him. The silent screams causes him to lose all his clothes.
- The Histeria! episode "The Thomas Jefferson Program" had a segment where the World's Oldest Woman portrayed Betsy Ross in explaining the origin of the American flag. The explanation given is that Betsy Ross got food stains on her bloomers and ended up having her bloomers run up a flagpole, leaving her wearing a barrel.
- KaBlam! anthologized the Life with Loopy episode "Lunar Loopy" where this was planned along with un-stranding an Astronaut.
- Phineas and Ferb: Buford does this to Baljeet in one episode when the group was camping in the woods. Phineas was also pretty sure that there was no flagpole, so Buford said he would be willing to settle for just stealing Baljeet's underpants. It's also implied Buford stole them off his body.
- Popeye and Bluto, who are living on a tropical island by themselves, spot Olive Oyl on a raft using her knee-length bloomers as a flag in "Shape Ahoy."
- In an episode of Recess, TJ and his friends remove the flag from the top of the Ashleys' clubhouse and replace it with Miss Finster's underpants.
- The Teen Titans Go! episode "Snot and Tears" begins with the Titans, and their new friend Bumblebee, paying giggling respects to Robin's underpants, waving majestically on a flagpole. The laughter abruptly turns to shrieks of horror when Robin emerges from his cabin without any.
- In an episode of Robotboy, Donnie Turnbull (Tommy's obnoxious big brother) does more than run kids' underwear up flagpoles. He does so with the kids still wearing them.
- While it's not shown, Duncan and Gwen from Total Drama did this in one episode after star gazing together and getting a little too close for friends. Gwen states that they did this after Geoff tries to imply they kissed. In a rare version of this trope, they ran everyone's underpants up the flagpole, rather then just one person.