Sometimes the border is marked by concrete walls, barbed wire, machine guns, attack dogs, and constantly roving searchlight beams. At other times it's merely a stretch of open water or wilderness, but still patrolled at regular intervals.
The Checkpoint Charlie version is when this crossing has to be made at an official border control station. In that case the protagonist better hope their papers are in order.
The real Checkpoint Charlie is now a tourist attraction.
- In the run-up to the 2006 FIFA World Cup, one commercial featured a man and pregnant woman driving through a border check-point. Just after the guard checks their papers and lets them through, the guards get a phone call. A voice yells, "GOOOOOAAALLL!!!" just as the "pregnant" woman lets a soccer ball fall from under her dress.
- Asterix: In Asterix in Spain, there is a huge traffic jam on the border between Gaul and Spain due to the Romans checking each carriage. Since they have Pepe, the boy the Romans are looking for, with them, Asterix and Obelix hire a guide to get them across the border without getting seen by the Romans.
- Total Recall (1990): Quaid has to go through immigration to enter Mars.
- Charlie Muffin (1979). Charlie's superiors set him up to be arrested when he crosses the Berlin Wall. Fortunately Charlie is suspicious and gives his papers to an East German hoping to escape to the West. The German panics when the arrest takes place and gets killed.
- Subverted in Monsters. When the protagonists arrive at the huge wall at the US border they find it abandoned, as the aliens have overrun it.
- Spoofed in the 1985 action-comedy Gotcha where the young protagonist has to run the gauntlet of Checkpoint Charlie's Obstructive Bureaucrats. He flips them the bird once he's safely through.
- Babylon A.D.. Vin Diesel has to cross the Bering Strait on a Live-Action Escort Mission, despite it being patrolled by Attack Drones that kill everything that moves (literally, the drones killed two polar bears).
- James Bond:
- In The Living Daylights, Bond arranges for a defector to cross the Czechoslovakian border twice — first by being shunted through a pipeline and on the second occasion by Weaponised Car. And a cello.
- Even more so, Octopussy partially takes place around the border sections near Karl-Marx-stadt (Chemnitz). 009 and General Orlov get killed trying to cross it.
- Stripes. An Army unit is accidentally led into Soviet-controlled Czechoslovakia. Some members of the unit break into the country through a poorly defended border outpost to rescue them, and break out again through the same outpost.
- Machete begins with a failed US-Mexico border crossing, serving to demonstrate the villain's complete lack of morals (and intelligence, as they capture the whole thing on film, with the US Senator helpfully identifying himself as he shoots a pregnant woman).
- Men in Black starts with K arresting one of the aliens trying to cross the Mexican border.
- The Debt. The main characters must cross into East Berlin, and then try to cross back.
- In Star Wars: A New Hope, Obi-Wan Kenobi gets his party through a Stormtrooper-manned checkpoint because those weren't the droids they were looking for and they didn't need to see their identification.
- The climax of Argo is one of these, made much more dramatic than it was in the real story. In this case the airport in Tehran serves as the border crossing.
- Congo. The expedition tries to surmount this problem by flying over the Zaire border, only to be shot down by army units armed with heat-seeking missiles.
- The Real Life Checkpoint Charlie is a critical locale in Bridge of Spies, as it is where American student Frederick Pryor is released, allowing the spy exchange to take place.
- In the climax of The Soldier, the title character has to drive through Checkpoint Charlie, but is recognised and pursued by a US marine who's encountered him before. Fortunately his Crazy-Prepared Mossad allies have set up a Ramp Jump so he can get over the Berlin Wall the hard way.
- The Spy Who Came In from the Cold opens with the Checkpoint Charlie version. It doesn't go well — the spy is gunned down right in front of the protagonist Alec Leamas. At the end an escape route is organised across the Berlin Wall, but the Love Interest is gunned down in a pre-arranged setup, as is Leamas when he goes back for her.
- Happens several times in the Quiller series, and often mentioned as a Noodle Incident.
- Ernest Hemingway's A Farewell to Arms. Frederic Henry and his Love Interest have to row across an Italian lake in a storm to Switzerland in order to escape arrest. They see a Guardi patrol boat, but fortunately it doesn't see them.
- Friday by Robert A. Heinlein. Action Girl Friday has to cross the Divided States of America. In one case she knocks down someone repairing a border fence, only for him to follow after her because he wants to escape as well.
- Game, Set & Match by Len Deighton. Bernard Samson is haunted by the memory of a friend who performed a Heroic Sacrifice while crossing the Berlin Wall, enabling him to escape. This scene is shown in the TV series, as is another incident in which a defector is smuggled across by lying in a coffin-sized box with oxygen feed in the bed of a dump truck, which is then filled up.
- Funeral in Berlin, also by Len Deighton, has a defector being smuggled by faking his death and being taken across the Berlin Wall in a coffin. The idea has been reused several times, such as in the TV series Jason King and MacGyver.
- The Dogs of War details how guns are smuggled across the French border — they can either take the random risk of a permanent customs point, or try a forest road that could be manned by a flying customs check that searches every vehicle. To reduce the risk they send another vehicle first; if it fails to return in a certain time, they know it's been stopped and searched.
- The Modesty Blaise short story "The Giggle Wrecker" has Modesty and Willie trying to sneak a Soviet defector past the Berlin Wall.
- We the Living by Ayn Rand ends with the protagonist being killed by a border guard as she tries to escape the Soviet Union.
- The Girl Who Circumnavigated Fairyland in a Ship of Her Own Making features a gnome as a border guard for Fairyland who enforces the entry requirements of the Marquess (including allowing Ravished humans in without a visa) and keeping out wind spirits who haven't been granted citizenship yet. She works from inside a kind of Steampunk gargoyle, since it embodies the authority that makes people willing to put up with customs inspections in the first place (and also doubles up to make humans a bit sensitive to the Glamour of Fairyland).
- The Sandbaggers has repeated crossings of the Iron Curtain. In one memorable instance in season 3, one of the main characters gets out of Russia on dodgy papers by going for his passport and accidentally-on-purpose showing the officials a sheaf of dirty photographs instead; they're too busy laughing at him to check his actual passport very thoroughly.
- One episode of MacGyver (1985) has a Cold Open in which Mac is attempting to get out of an Iron Curtain country concealed inside a coffin.
- MythBusters tested a myth where illegal border-crossers attempted to use a giant portable slingshot to fling people over the U.S. border. The reality of the situation was that any device that could fling a person as far as the myth stated (300 yards) would have to be implausibly large and not portable at all (the MythBusters version, which used radio towers, couldn't fling a person that distance), and that doesn't even get into the injuries the people would suffer in making the transition. Long story short: myth Busted.
- In an episode of Mission: Impossible, one of the agents (Barbara Bain) is captured in East Berlin. After she is tortured and tells them nothing, the team's leader (Peter Graves) manages to talk them into releasing her. He gives her an overcoat against the cold and they start across to West Berlin when the Germans behind them open fire with machine guns, apparently killing them. They are quite satisfied that it no longer matters who they were or what they were after. When it is clear the agents get up and he explains that he anticipated that and used bulletproof coats. She laughs and says "I thought it felt heavy."
- In White Rabbit Project the team construct a hot-air balloon from scrap metal and sailcloth based on a tale of an East German family escaping over the Berlin Wall that way. They fared much better than the Mythbusters border catapult, as not only did the reconstruction work properly, but the research confirmed that the real people made their escape.
- A 1983 TV movie Love Is Forever is the Based on a True Story of an Australian journalist who helped his Laotian wife escape her country by having them swim the Mekong River underwater using scuba gear. This is pretty dangerous even before the border guards start shooting at them; there's a strong current that makes it impossible to swim directly across and carries all kinds of debris, and thanks to the dirty water you can barely see where you're swimming and thus might not see an object before it hit you.
- The Man in the High Castle: In season 2, Juliana Crain realizes that she's no longer safe in the JPS and defects to the Reich by crossing a border checkpoint at their San Francisco embassy. The Kempeitai troops standing guard attempt to stop her when they see what she's doing, but she manages to cross safely.
- Shadowrun. Several adventures feature the runners having to pass through heavily defended borders, either through force or guile.
- Hero Games
- Top Secret module "Operation Fastpass". The spy PCs must help a defector escape from behind the Iron Curtain. In order to do so they must get across the border into friendly territory.
- The Call of Duty: Black Ops multiplayer includes a level named "Berlin Wall", based on the Trope Namer, where the Soviets have abandoned subtlety and smashed the wall with tanks.
- Papers, Please is a game all about playing a faceless official manning one of these in a fictional Communist nation. With the extra tip of the checkpoint being between East and West Grestin.