"Shaken, not stirred, will get you cold water with a dash of gin and dry vermouth. The reason you stir it with a special spoon is so not to chip the ice. James is ordering a weak martini and being snooty about it."
— President Bartlet, The West Wingnote Bartlet has forgotten that James orders vodka martinis
Everyone knows this character. He wears a tuxedo with a small Bowtie (which Is Cool), a martini in one hand (shaken, not stirred, naturally) and a Walther PPK in the other. Announcing himself as "Surname... Forename Surname", he engages in witty Double Entendre speak with busty high society women that leads into the bedroom. And just in case he finds himself in a particularly hopeless situation, he'll have a gadget hidden in his cuff links that will allow him to defeat the mooks (with a bad pun or two thrown in posthumously) and save the day.
The character that should have immediately come to mind with that description is, of course, James Bond. However, while Bond has definitely popularized many of these aspects, most Shallow Parodies out there can't seem to find anything beyond the above paragraph to make fun of (They also seem to miss that Bond typically wore situation-appropriate attire during field work).note One annoyingly common mistake is for the parody character to get a gin martini instead of a vodka martini (as the otherwise-valid opening quote shows: it's a potentially-legitimate concern with a gin martini, but with a vodka martini using vodka made from potatoes, the shaking gets rid of some nasty-looking oils on top. And Knowing Is Half the Battle!). It's also interesting to note that most of these tropes were NOT in the Ian Fleming books. For example, the films inverted his usual stirred-not-shaken Drink Order. Nevertheless, this is how James Bond is viewed by and large.
Contractually guaranteed to show up in everything that has to do with secret agents from ~1963 onwards. Exceptions are almost noteworthy in their own right, although there is the alternative trope of "Stale Beer flavour" Spy Fiction.
This outfit is used to indicate an international spy figure in much the same way a Conspicuous Trenchcoat is used to indicate a spy or detective in a more urban environment.
As so many of these characters could be seen as placeholders for James Bond, this whole page could be considered his character-specific subtrope of Fountain of Expies. See also Dead Unicorn Trope
xXx was essentially one big Take That against this trope, and opened with one such agent being easily tracked down and killed because his tux stood out in the heavy metal concert he tried to escape through. Then used again where Darius had to dress up as a waiter at a party. The disguise works well enough to hide him amongst a lot of other guys when they were on to him.
Clark Devlin in The Tuxedo is almost never seen without his tux. He's smooth with the ladies and dances very well. Slightly subverted in that most of that is due to the tux being a highly-advanced piece of technology that does most of it for him. He is seen without his tux at the end, on the roof with a sniper rifle wearing something a SWAT member might wear. He is never shown in action, though.
Done in at least one scene per movie in the Mission: Impossible series. In fact, the opening of the very first movie involved the heroes in tuxedos.
In Planetary, the character of John Stone is a clearly a James Bond Expy. In issue #11, he employs fantastic gadgets and tosses out one Bond One-Liner after another while facing a villainess who has just shot his assistant - who was an Expy of Nick Fury!
The League of Extraordinary Gentlemen: Black Dossier, has a Deconstruction. Bond himself appears (with the serials scratched off— his name is only given as "James", but we're also told he's related to Campion Bond)... and he's an attempted rapist who gets the crap kicked out of him after some jokes about a woman's stage name being Oodles O'Quim. He's kind of an ass even beforehand, so this is very satisfying. Unfortunately, we see him walk off with the girl in the end, after he murders her adoptive uncle, who had exposed him as a traitor. Alan Quatermain even mocks how sorry the British adventure hero had become.
In Subversive Activity, Reddon (only his love interest calls him "James") wears evening dress, carries useful gadgets, expresses an appreciation for a vodka martini shaken not stirred, and appears constitutionally incapable of leaving an entendre undoubled. He also has a justification for wearing evening dress while breaking into the opponent's lair: at first he just says it's "rather a tradition in my service", but later he elaborates that because he and his secret service colleagues all dress that way when they go to work, it is de facto the uniform of the service, and therefore if he is captured by the enemy he can claim honorable treatment as a uniformed serviceman under The Laws and Customs of War and avoid being shot out of hand as a spy.
In Death: Roarke comes pretty close to this trope. Divided In Death had Peabody pretty much refer to him as an Expy of James Bond.
Star Trek: Deep Space Nine. Bashir likes to run a holosuite program that enables him to basically BE the film James Bond. "Bashir, Julian Bashir." He also specifies his martinis "stirred, not shaken" to invert Bond's usual drink order. Lampshaded all the way by Garak's constant snarking about it, when he was along for one run of the program (When something weird happened, of course). Despite the presence of an honest to goodness secret agent in the program, Bashir ignores him because he's playing James Bond, and is not in an actual covert operation, and the two play by different rules.
Garak (on having it explained to him that the decadent living and Bond Girls are government-issue): "I think I joined the wrong intelligence service!"
Parodied in That Mitchell and Webb Look with 'Agent Suave', who has a Casino Royale-style adventure in a high-stakes casino where all the games are typical village fete things like 'guessing the weight of a fruitcake' and 'whack the rat'.
M Expy: And, Suave... good luck. Suave: I won't need luck. M Expy: You're going to a casino. Suave: Oh, God, yes, that's right. Blimey. Fingers crossed!
The same sketch also subverts the one-liners: it quickly turns out Mission Control provides them. For both Suave and the villain.
Played with a lot in Chuck. Chuck Bartowski is the furthest thing from James Bond you can find. But he still tries, because he's Functional Genre Savvy. When he evolves from The Woobie to Iron Woobie, he makes it work. In fact, because he's so successful (thanks to Casey, Sarah and the Intersect) that the default name he uses when he goes on a mission becomes feared by the enemy agents as a Bond-esque Tuxedo super-spy. Bryce Larkin, in the early episodes, highlights the 'international superspy' as he should be, and Roan Montgomery basically IS Bond, if he were allowed to genuinely age.
Mythbusters tested out if you could wear a tuxedo under a dry suit to crash a party on a yacht. After swimming underwater for half a mile, Jaime came up out of the water, stripped off the dry suit, and was able to attend the party in a perfectly presentable tux.
In one scene in Rayman 3: Hoodlum Havoc, a Hoodlum dresses in a tuxedo and holds a gun in the classic James Bond poster pose, before throwing it aside and pressing a button on his arm, which produces a ridiculously large mechanical device, which fires a laser beam that turns an unfortunate caterpillar into something resembling a roast turkey.
The Spy in Team Fortress 2. Impeccable three-piece suit (that can now come with a bow tie), upper-class speech patterns and haughty mannerisms (that is, when he isn't given to childish insults), wears a fancy wristwatch with a built-in cloaking device and all sorts of other fancy gadgets. Promise not to get blood on his suit and he'll kill you quickly.
If one plays Metal Gear Solid enough times, Snake will do this with a Tuxedo instead of his trademark Spy Catsuit. And damn he does look fiiiine in a Tux.
Playing Metal Gear Solid 3 while wearing the Tuxedo nets Naked Snake an amusing and annoyed lecture from The Boss about how impractical it is. There's also a conversation about James Bond with the other characters (specifically the Major, who is a complete James Bond fanboy) suggesting silly things (like a gun shaped like a snake) that he could use.
The Spy in Command & Conquer: Red Alert appears, at least to the Allies, as a man in a dapper (if combat-inappropriate) tuxedo-and-bowtie; selecting him or giving him an order causes him to reply in a Connery-ish voice. Of course, to opponents (i.e., the Soviets) he looks like one of their own units, unless discovered by a guard dog.
Harry Tipper of TimeSplitters. In the second he is strapped to a bed with a laser aimed at him...
Secret Agent Clank, the character that Clank plays on television as his day job in later Ratchet & Clank games, is an obvious James Bond parody.
Inverted by Spy Party, where Spy players are least likely to choose this outfit as the spy, presumably because they expect the sniper will be suspicious of that character.
John Steele, the British super-agent in Evil Genius, is an obvious James Bond parody, showing up immaculately dressed to invade your Island Base. He is also the toughest enemy in the game.
SPY Fox, while he doesn't drink or wield a gun, is a blatant example. He uses the line "shaken but not stirred" to describe himself being jostled, which happens to him often in his line of work.
Good Hitler in Goats, e.g. here. Note tuxedo, martini; the "last, first last" introduction may not have been included, though. In fact there's an entire Good Hitler franchise in the Goats verse, replacing not only Bond flicks ("Die and Die Again", "Death Never Lives Twice", "Quantum of Hitlers"), but almost every other known movie ("Good Hitler vs. Space Hitler", "The Search for Good Hitler").
Sluggy Freelance: In December of 2001 the strip did a James Bond parody called Snowfinger. After Santa Claus is mutated into an alien hybrid, Bun-bun is recruited by the Christmas elves to stop Santa from distributing presents laced with alien mutagenic spores.
Agent 300 started out as a Shallow Parody of Bond, used in his introductory comic to prove how useless a character like that would be in a confrontation with Niels. However, his author liked him so much he inexplicably recovers from the head wound Duncan deals him in that strip and quickly becomes a much more fleshed-out Break-Out Character.
The fan-made spinoff comic Secret Agent Men has fun playing with this trope as it more fully explores the agency 300 and 250 work for.
Derek Blunt on Darkwing Duck. Although he dresses and acts to fit the Bond stereotype, Blunt unusually eschews gadgets and tricks in favor of realistic spy work.
One episode of ReBoot spoofed this type of character with "Matrix, Enzo Matrix", as well as Wacky Races.
Archer, a total Jerk Ass secret agent with massive mother issues, lives the trope — notably, he puts off defusing a bomb to change from his tuxedo to a black turtleneck. It's portrayed in a kind of Bunny-Ears Lawyer way; his flair for the dramatic and fondness for women and alcohol constantly get him in trouble, and he's incredibly irresponsible with the safety of anyone around him, but much like Bond, when it comes to hand-to-hand combat, firefights, and other So Much for Stealth stuff he's practically a superhero.
Phineas and Ferb: "Elementary, My Dear Stacy" takes place in England. Because of a prior incident with the union, Agent P works with Agent Double-O O. The latter takes hours to burn through a manacle, while Agent P simply gets the key off a table.
Pinkie Pie: Or as he's known in the spy world, Mane. Con Mane.
Dusko Popov was a Yugoslav who worked for British intelligence (and convinced the Germans he was spying for them while feeding them false information) during World War II, mostly as a way to live large and have love affairs on an expense account. He worked with Ian Fleming and one of his exploits at a casino in Portugal may have inspired Casino Royale.