Friend in the Black Market

""It's hard to get the things, besides there's a war on.""

You're in a sticky situation; you need to get something and there doesn't seem to be a legal way of getting it. (It could be banned, rationed, from overseas or possibly just made in extremely limited quantities). If you're lucky, you'll have a Friend in the Black Market.

These guys are the real deal, never dealing in substandard goods because that wouldn't be good business practice and they rely on their reputations. They don't ask any questions either. Their main vice is that they're going to ask for a fair bit more than what the item is worth. As shown by the page quote, their defense for this is that it's the circumstances and the effort to get the items that makes them charge the prices, but often it's also a bit of avarice too. (Which often makes them Mr Vice Guys.)

Personality wise, like Honest John, they can fit anywhere into the Character Alignment spectrum. (Although the fact they deal in quality products usually puts them at least chaotic neutral.) If the character is part of the main cast, then they'll usually be Chaotic or Neutral Good. In a war situation, they also tend to screw it and party, unless the action is centered on the military in which case they'll be doing this work on the side.

Compare and Contrast Honest John's Dealership who also sells products at a premium... except theirs are of lesser quality. The Scrounger is likely to either be this trope or to have dealings with him.

Comic Books

 * The Penguin could fit into this trope; while his main merchandise is information for Batman, he also does a lot of shady business. Because Batman's a poor tipper.
 * Al Capp's Li'l Abner had Available Jones, who could provide anything from a safety pin to a battleship, for a price.

Film

 * Nick and Fetcher from Chicken Run. They only work for you if you pay them in eggs, but they're very skilled at stealing the items you need.
 * The Shawshank Redemption: Red is able to get, amongst other things, a poster of Rita Hayworth and a small rock hammer.
 * Flash Harry in the St Trinian's series.
 * Sid Carter in Carry On Matron.
 * Sgt. Bilko in Sgt Bilko
 * Joseph in Au Revoir les Enfants

Literature

 * Recurring character Bubba Rogowski of Dennis Lehane's Kenzie and Gennaro Series is a former Marine who specializes in obtaining lots of illegal weapons and tech, and has put lives mines through his entire warehouse apartment to deter unwelcome guests. He's also something of a Psycho for Hire and a Man Child who can barely read, but he's been friends with Patrick since they were kids and will kill anyone who messes with him.
 * Mundungus Fletcher in Harry Potter and The Order of The Phoenix starts out this way, as the guy brought in to help the Order get information on dark dealings (and to get the Weasley twins illegal goods), but his role in the story develops.
 * Rhett Butler from Gone with the Wind, who lives quite well despite the late unpleasantness. (He is a privateer, after all.)
 * In Neuromancer and it's two sequels, there's "The Fynn", a blackmarket dealer that appears regularly to sell equipment and information to the protagonists. Due to the nature of the depicted cyberpunk society, it's debatable wether he can be considered a friend, though.

Live Action TV
""You'd be surprised with what a priest can get away with.""
 * Private Walker, the spiv in Dads Army.
 * Both Radar and Klinger from M*A*S*H (television), who use their wits to get anything the hospital needs. (Klinger getting the job when Radar leaves)
 * And when that didn't work, more than a couple times Father Mulcahy was the go-between between the camp and the actual black market.

"Barney: And, if I don't have a guy for something, then I have a Guy Guy to get me a guy. And, oddly enough, his name is Guy."
 * G'kar deals with... not really a friend, but a man he knows who deals in black market weaponry, which he needs for the resistance on Narn. The dealer is selling him for far more than the weapons are worth. G'Kar should know, because he sold many of those very weapons to Earth during the Earth Minbari War fifteen years earlier. In this case, the quality of the merchandise is guaranteed with the understanding that what G'kar will do to the dealer if it isn't will be unpleasant.
 * In Firefly, the crew of Serenity tend to work for this guy (or a variety of these guys), using their skills and ship to acquire the goods for the market. From time to time, they will be seen doing business of their own with these sorts when they need to get things like disguises for their heists.
 * In one episode of Space: Above and Beyond, Captain Vansen is forced to deal with this guy aboard the Saratoga, trading him a key to the Officers' Lavatory (presumably much nicer than what the enlisted guys normally get to use), in exchange for a bowl of strawberries that she needed to trade with someone else to get his spot in line to make a call home.
 * Sgt. Bilko in The Phil Silvers Show
 * Dorium in the Doctor Who episode "A Good Man Goes to War". He starts out working for the villains, then learns that they've kidnapped  and decides to run for it before the Doctor turns up, knowing how many people owe him favours. As it turns out, he's one of those people, and is drafted into the Gondor Calls for Aid scenario.
 * Barney from How I Met Your Mother "has a guy" for just about everything, from a "Suit Guy" and a "Whip Guy" to a "guy in the DA's office" who "scored us front row seats to a lethal injection!"

"Lily: You always say you "know a guy". How many guys do you know? Uncle Eddie: I know about 75 guys."
 * In Seinfeld Kramer's unseen friend "Bob Sacamano" provides many obscure, black-market products - from counterfeit Russian "rat hats" to "The Wizard" Tip Calculator for the condo association (which may be hot!). He is said to have made a fortune for having invented the "paddle with ball" toy, being the first one to attach a rubber band. Before that, Kramer insists, people would hit the ball and it would just fly away.
 * Uncle Eddie from Grounded for Life has a lot of connections with suspicious people, and is often able to obtain questionable items. Pointed out in one episode:


 * Peter from Fringe has plenty of these.

Radio

 * CPO Pertwee in The Navy Lark

Video Games

 * This arises as a gameplay mechanic in an awful lot of video games (especially RPGs) where the shopkeepers expect the heroes to cough up the dough even when the world is about to end. After all, Adam Smith Hates Your Guts. It fits this trope more than Honest John as at least they sell you legitimate items.
 * Except that little snotrag Wirt.
 * The Spyro the Dragon series has Moneybags, who will perform various services for you for, "* ahem*, a small fee." It's usually anything but small (not to mention sometimes the price is insane for what he does), but if you want to finish the game, let alone get 100% Completion, you'll have to pay up.
 * You.
 * Ratchet can buy a lot of black market gear during the course of his adventures, from weapon mods to hypnosis gadgets to giant overpowered weaponry.
 * Drebin in Metal Gear Solid 4: Guns of the Patriots is named for The Naked Gun character due to what he sells; 'naked guns' - the arms he sells are not ID-Locked, and so can be used by anybody, which comes in very handy for Snake. Also plays the Big Damn Hero at times, and serves as Mr. Exposition in relation to the backstories of the Beauty and the Beast Corps.
 * In Red Dead Redemption, Irish and Seth are this for Nigel West Dickens. Of course, West Dickens is a Snake Oil Salesman.
 * Krew is this in Jak and Daxter to the Underground but he;ll sell them out if the price is high enough.

Webcomics

 * In Order of the Stick, Haley was able to arm La Résistance in Azure city by purchasing smuggled weapons through the black market.

Web Animation

 * While Bubs of Homestar Runner may mostly be an Honest John's Dealership, he also sells stuff on the black market—and his black-market merchandise are more legitimate, higher-quality products than anything he sells at his store.

Western Animation

 * Hustler Kid in Recess. In one episode Gus became the "Gusler Kid" and did even better than him. TJ also went a bit mad when an Expy of Pokémon cards was adopted as a currency of sorts.
 * In Aqua Teen Hunger Force Carl has a friend named Terry. Terry can get things...but you don't want to know where he got them.