Incredibly Obvious Tail

Black clothes? *Check*. Sunglasses? *Check*. Binoculars? *Check*. Walkie-talkie? *Check*.

"The good news is if you know you're being followed , they're probably just trying to intimidate you. The dangerous ones would be those that you don't know are following you."

—British Embassy Worker, Them, Adventures with Extremists

Whenever a character is being tailed, the pursuer will be very obvious to the prey if the prey would only look behind himself/herself. Occasionally this is done deliberately, if the authorities want the suspect to know that they're onto him so that he won't do what he's thinking of doing.

This occurs in a variety of genres, but is most telling in espionage and, to a lesser extent, Crime and Punishment Series, as both the pursued character and the pursuer should have a rudimentary knowledge of surveillance and counter-surveillance.

Note that advanced stories have clever spies use two tails. One is obvious and when the person being tailed shakes them off they are too busy feeling smug to notice the other skillful tail. Other stories avoid this trope by using a Tracking Device on the subject, allowing the followers to follow them much more subtly, unless they discover it of course.

Not to be confused with the thing cat-girls have. Or that thang J-Lo has, either. Compare the Incredibly Obvious Bug.

Examples of Incredibly Obvious Tail include:

Anime and Manga

In one episode of Ghost in the Shell: Standalone Complex, Togusa has radio dialog indicating there's another car that should be swapping off with him, the way a real tail should work, but it immediately cuts to a scene of him turning off the freeway directly behind the target, and the other car is never seen or mentioned again.
- ...and he is spotted by the people he is trying to tail. It wasn't obvious only to the audience.
In Mahou Sensei Negima, when Asuna and Negi tailed Chachamaru with the intention of recon/defeating her, they went between this and a perfect tailing; they hid behind corners and in bushes when needed, but then trailing after her in wide-open roads and clearings. The robot didn't manage to notice till confronted. Interestingly, the series' many Date Peepers are quite good at tailing.
In Death Note, Raye Penber did this, and unfortunately for him he was spotted.
Full Metal Panic!. Despite being a trained professional, Sousake Sagara fails completely in his attempts to covertly follow Kaname Chidori to guard her from kidnappers, as his nature makes him competent on the battlefield but knowing nothing about how to act like an Ordinary High School Student. Such as jumping from a freaking train. While it's moving. "I wanted to get off at this station, it had nothing to do with you."
An early death in Case Closed happened while Kogoro was acting as the obvious tail to a victim who seemingly inexplicably turned up murdered.
- Correct tailing methods are mentioned much, much later when Conan realizes that the car behind them was a tail because they didn't honk when his mother lingered to long at a light and then the driver eventually started smoking, signaling that he'd given up the case.
A Certain Scientific Railgun: Kuroko following anybody, Misaka and Kuroko tailing their dorm supervisor.
Fullmetal Alchemist Ed and Al noticed a huge guy in a trench coat trailing them in a not so subtle way.
In one episode of Sailor Moon, Usagi tiptoes down the sidewalk after an increasingly annoyed Chibiusa. When she finally whips around and calls her out on it, Usagi leaps behind a pole several seconds too late to even pretend she wasn't seen.

Fan Works

In Kira Is Justice, Sol notices his tail, a SIS agent named Ronan, due to his good observant skills. Sol then tells Justin, who he doesn't know is Kira.
In chapter 2 of Drunkard's Walk VIII: Harry Potter and the Man from Otherearth, protagonist and part-time narrator Doug Sangnoir notes that he is being followed through Diagon Alley:

It was on my way to the Cauldron that I realized that I was being followed. It was hard not to -- my tail was a pair of burly wizards in black robes who stalked me with all the care and subtle tradecraft of a drunken bull. Their every motion in passing through the crowd behind me amply demonstrated that to them, stealth was a concept that applied only to other people.
In a culture with Disillusionment spells and invisibility cloaks, *this* is how the two of them decide to follow someone? Feh. Amateurs.
Gods save me from having to deal with freakin' amateurs.

Film

Sherlock, Jr.: Buster, when the book said "Shadow your man closely", it didn't mean that closely.
Various James Bond films.
- Justified in From Russia with Love, because the British and Russian agents tail each other as a matter of course, and no secret is made of it.
In the 1980 war film The Sea Wolves, Roger Moore carries out a ridiculously unsubtle tail of a German agent (as he's doing it in India he particularly stands out).
The French Connection (1971) goes to some trouble to show how a real life tail should be conducted (even so Gene Hackman's character is successfully evaded by the Frenchman on the subway).
White Heat (1949) starring James Cagney shows how a vehicle tail is conducted.
Bullitt's famous Chase Scene starts out with this, including the chasee's Perfect View of their rear-view mirror as the Forest Green '68 Shelby Mustang GT Fastback crests the San Francisco Hills.
Lampooned in Loaded Weapon 1, where the villains are following a car so closely they're in the back seat.
Ruthless People. The crook picking up the ransom money is followed by a long line of unmarked cop cars before he drives off the jetty.
McQ (1974). John Wayne (following directly behind in a green Pontiac Firebird Trans Am) tails a Bureau of Narcotics van carrying $2 million worth of confiscated drugs to the top secret location where the drugs are to be burned.
Done in Back to The Future 2 for laughs. Doc tells Marty to be inconspicuous when trailing Biff; Gilligan Cut to Marty wearing a black leather jacket and a fedora as he follows Biff (who, true to the trope, doesn't realize he's being followed until Marty gets right up in his face).
Sin City has Bruce Willis and Jessica Alba being tailed by a hideous yellow man in a British model car (the steering wheel is on the opposite side). Needless to say, they notice.
In Mitchell, Mitchell is assigned to stake out James Arthur Cummings, parked across the street from his house. When Mitchell decides to go up to him and tell him he's staking him out, he appears not to have known about it. At one point during the stakeout, Cummings invites Mitchell in for dinner, and soup-related Hilarity Ensues.

Literature

In Robert Asprin's Mything Persons, Skeeve and Co. pick up a tail so obvious that Skeeve's bodyguard Guido doesn't bother to say anything about it because he assumes they already noticed. Skeeve has to resist the urge to shriek at him when this comes up, particularly when it occurs to Guido that their follower could be part of the aforementioned double-tail gambit. (She's not, as it happens.)
In The Drawing of the Three, Eddie Dean plays host to Roland's consciousness. Eddie is suspected of smuggling drugs into the country, and several DEA agents are tailing him. Eddie notices the obvious ones, and Roland picks out the rest.
The Berlin Memorandum by Adam Hall. The neo-Nazis release Quiller in the hope of following him back to his base. As he knows he's being followed anyway, the Nazis don't bother hiding themselves, as Quiller is working against the clock and has to contact his superiors regardless.
There are multiple versions of this in The Thrawn Trilogy. In Dark Force Rising, a bounty hunter gets Mara's attention with a tail who was wearing something unusual. In Heir to the Empire, Han Solo met with an old smuggling contact, who snidely noticed that Wedge Antilles, seated at a nearby table, was the most obvious backup ever. After the smuggler left, we see that that was the point, and the other backup, the commando Page, was unnoticed. Even later in the same novel an Imperial tail is actually described as being very good at what he does; problem is, he's tailing a Jedi who senses him easily.
- The bounty hunter in particular was his own obvious tail; as soon as she spotted him he disappeared (to get her to follow him), killed a random passerby, dressed the corpse in his unusual attire, and positioned himself to ambush her ambushing the corpse posed to ambush her.
Going Postal has one, with the note that "If you saw Vetinari's spy, it was a spy he wanted you to see."
- Which Vetinari confirms. He deliberately sends a clerk who is unskilled at surveillance, explaining that he would like the target to become "a little more nervous" to provoke him into rash actions and mistakes.

Live-Action TV

Parodied in an episode of Psych, when Shawn shows Gus a series of pictures of a very conspicuously half-hiding man following him.
Commonly used in The Wire. Sitting in a parked car 20 feet away with a pair of binoculars and a partner. 5 guys on a roof with the world's biggest camera... Notably one of the few times they try to tail someone in a car he catches on almost immediately, and wags his finger at them.
In the first episode of the British spy drama The Sandbaggers, the main characters easily spot that they're being followed by Norwegian agents on a training exercise.
Thomas Magnum whenever he followed someone in his very obvious red Ferrarri in Magnum, P.I..
Played with in an episode of Walker, Texas Ranger when Walker and Trivette are playing security guards on an armored car they're tempting the crooks with. Initially it's subverted (in reverse) when the crooks are snickering at the incredibly obvious Rangers pretending to be guards, but in action with the Rangers who are apparently oblivious to the large SUV that's been following them around all day. Quickly reversed when Walker and Trivette secretly switch trucks to one the crooks think it a good target, and Walker asks if the SUV is still following them.
Averted in a Burn Notice episode where Michael is trying to follow his mark. He recruits the help of Fiona and Sam in their own cars. Each follows the target for a bit, while maintaining radio contact with each other, before swapping with the next follower. This way, no one car is constantly following the mark.
- In other episode, the tail (Michael's ally) is obvious and overconfident enough that the prey leads him into a roadblock.
Dexter has this all over the place. Dexter, as an experienced serial killer, presumably has mad stalking skillz, but some of the tailing he does would be obvious to anyone—and he's usually stalking other seasoned killers, too.

Video Games

The spy class in Team Fortress 2 if the player is just that bad.
- If you're on their side. If you're not, then they're only that bloody obvious if uncloaked or undisguised. This troper has had enough nasty experiences with them to know. My suggestion is to keep somebody with a flamethrower handy.
Certain missions in the Grand Theft Auto series, which requirs you to drive maybe three car lengths behind, no closer, no further away. If the guy you're tailing stops at a traffic light, the correct response is to stop ten metres behind him in the middle of the road. He will think this is completely normal.
- This mechanic gets passed on to the True Crime games.
Hard to tell what's going on with this trope in Assassin's Creed. Either you are legitimately following your targets on the ground, or you are running on rooftops and can possibly draw attention.

Web Comics

Seen in Homestuck here. Seriously, how could you not notice that was following you?

Web Original

In Red vs. Blue: Reconstruction, Agent Washington is tasked with pursuing the Meta. Starting in Episode 3, the audience learns that the Meta is in fact pursuing Wash instead, and often at close range (at one point, he hitchhikes on the back of Wash's tank). Turns out Wash knew from the beginning that he was being pursued, and was in fact counting on that to lure the Meta into a trap.

Real Life

Internal security services will sometimes use an Incredibly Obvious Tail as a means of intimidating foreign spies or local dissidents. During the Cold War the KGB in Moscow used a technique called "bumper locking" where they'd stay only inches away from the car being followed.
- The same thing happened at sea. Dedicated Russian ships designed for the purpose would latch onto any American warships they came across and follow close behind, hoping to snatch up any floating papers the warship leaves behind for possible intelligence and to intercept radio transmissions. Though almost all Navy broadcasts are encrypted, it still behooved American commanders to limit traffic out of caution, which made the whole exercise a tension-building annoyance. Likely the tactic was used as a disruption to throw off normal plans with the outside chance of getting lucky rather than out of a genuine hope of gathering useful intel.
One of the classic tailing tricks used against people who know that it's likely they'll be tailed is to send two people - one relatively obvious and one extremely discreet.
In Germany there are a few cases of child molesters being set free due to legal technicalities despite being considered extremely dangerous. Police decided to place them under surveillance 24/7 which means that they now have a very obvious tail of at least 2-5 policemen in civilian clothes whenever they leave their home. Of course police go out of their way to be as unsubtle as possible so that their target doesn't forget even for a second that they watch his every move.
Several travel tales by adventurers in exotic countries report among their adventures constantly seeing the same guy behind them who is obviously a local security agent.