Number Two (slang noun):
Number Two for Brains combines both meanings: the first applies to the position, the second to the skull's contents.
In other words, this is when the one who has authority over the others, gets orders from and reports directly to the boss, and has to keep everything running smoothly is a moron.
Usually Played for Laughs and a sure sign that the guy in charge is truly Surrounded by Idiots. Compare Brains and Brawn, where the (possibly) stupid sidekick doesn't hold a position of authority. See also The Dragon, The Lancer, Number Two, The Igor, Pointy-Haired Boss, and Underling with an F in PR. May be The Starscream, but is virtually never Dragon-in-Chief — unless his boss is even more of a dingbat. Very often falls under Dumb Muscle. Overlaps with Vile Villain, Laughable Lackey in cases where the boss is noticeably more serious. Contrast Hypercompetent Sidekick, which often diametrically inverts this trope by being paired up with an inept boss instead. If the bad guy has two subordinates who happen to be idiots, then it's Bumbling Henchmen Duo.
- Mobile Suit Gundam: Iron-Blooded Orphans: As a fellow Seven Star, Iok Kujan is technically second-in-command of the Arianrhod Fleet and right below Rustal Elion in their hierarchy, but the reason he's The Brute rather than The Dragon is because of how utterly incompetent he is.
- One Piece has Hatchan to Arlong, who's so stupid he accidentally catches the seat of his own pants while fishing without realizing it, and is tricked into letting Arlong's prisoner Zoro go. Interestingly, he gained some IQ points after his Heel–Face Turn and is able to be Mr. Exposition for the Sabaody Archipelago arc.
- Otis in Superman: The Movie is a plump, bungling sycophant and flunky, whose only noteworthy skill is to make Lex Luthor's criminal genius all the more evident by comparison. He can't even be trusted with the security of their subway hideout: Lex sees someone tailing Otis on hidden camera and mechanically shoves the man in the path of an oncoming train, then berates his henchman, saying it's not the first time he's ignored someone following him. When Luthor reveals a map of his "new" Western Seaboard, he notices Otis has scrawled "OtiƧBURG" — yes, backwards S included — on an empty bit of land in marker, and demands it be removed. Interestingly, while he could more accurately be called a third-in-command behind the more valuable and skilled Eve Teschmacher, Otis is also Lex's direct subordinate because of how small their gang is.
Luthor: Bye-bye, California; hello, new West Coast — MY West Coast.
[Otis takes the plastic partition away, showing a reduced California coastline]
Luthor: Costa del Lex. Luthorville. Marina del Lex. Otisburg...
[He realizes what he's just said and turns to look at Otis in sheer contempt]
Otis: [feebly] Miss Teschmacher, she's got her own place...
Otis: [trying to defend himself] It's a little bitty place—!
Otis: [sounding close to tears] Okay, I'll just... wipe it off, that's all... just a little town...
- Hedley Lamarr's flunky, Taggart, and in turn, his flunky, Lyle, in Blazing Saddles.
- Wendell in Tricky People.
- Mr Pope from The Eiger Sanction (1975)
Pope: My superior wants to see you.
Hemlock: Your superior? Well that doesn't limit the field much, does it?
- Game of Thrones: Ramsay. As his more intelligent and self-controlled father's Number Two, he makes several stupid decisions due to his sadistic and impulsive nature. He ruins Theon to a point that he can't be used as a bartering piece with the Greyjoys, flays the Ironborn reavers at Moat Cailin rather than honor the conditions of the surrender, flays lords who refuse to pay their taxes, and holds a large feast for himself when Winter is Coming. In general, his sadism and impulsivity prevents him from waiting or devising non-violent solutions and consequentially, Roose spends Season 4 and 5 having to deal with his bastard/son's messes.
- In Weeds, U-Turn spent a great deal of time chiding his friendly but incompetent underling Marvin, eventually pushing him over the edge.
- Moriarty in The Goon Show is the dumber member of the (usually) villainous duo, with Grytpype-Thynne as the brains.
- Conroy Wu from Sleeping Dogs (2012) is the embodiment of this. He is the second-in-command of the Water Street Boys led by Winston Chu, but he is so much of a thuggish, ill-tempered, steroid using, and violent idiot that he makes his boss look worse rather than better by comparison, and as Charles Ho notes, represents Winston's inability to attract raw talent in the eyes of other Red Poles.
- Tropico gives us Penultimo, your second-in-command who is utterly loyal but not too bright.
- Uncharted 2: Among Thieves gives us Harry Flynn, who pulls a Face–Heel Turn early on, and demonstrates an outstanding lack of common sense more or less continuously, as well as deduction and decryption chops that would not shame a watermelon (although it's a bit unfair when the competition is Nate Drake). Sadly for him, the Big Bad is also a Bad Boss.
- In Biker Mice from Mars, given the limited budget available to him from the council of Plutark, Greasepit was probably hired by Limburger primarily because he was cheap. It's sure as heck not because of any competence on Greasepit's part. A flashback shows that Greasepit got the job because he had a good agent, or at least that was Karbunkle's excuse for not getting anybody better.
- Beast Wars: Scorponok fits this trope to a T. He was really kind of an idiot; really the only things he had to his name were his loyalty and some surprising talents with inventing (though when his inventions went wrong, they went wrong). To be fair, his loyalty certainly was a commodity what with the likes of Terrorsaur and Tarantulas on board.
- Since his selection is limited, The Brain from Pinky and the Brain has to rely on Pinky a lot in his schemes. This is frequently their undoing — almost as frequently as Brain's own overconfidence.
- South Park features Mimsy, sidekick to Nathan. Occasionally subverts it by being a little more sensible every now and then.
- Larry, Rippen's loyal but moronic henchman in Penn Zero: Part-Time Hero. There have been many occasions where Rippen would have easily won if not for Larry screwing everything up at the last second.
- Several episodes of Kaeloo have Stumpy act as a sidekick to Mr. Cat, and whenever he does this trope comes into use.
- The Wacky Adventures of Ronald McDonald:
- One-Eyed Sally's first mate Blather in The Legend of Grimace Island. One-Eyed Sally in her own words orders Blather not to think because he isn't good at it.
- In the final video The Monster O'McDonaldland Loch, the villain Stiles has a stupid henchman named Pip, whose idiocy ends up foiling Stiles' attempt at making Pip the fall guy when they are apprehended by police.