The Sneaky Guy

The Sneaky Guy is the one in a group who searches things out, looking for traps, enemies, and other hidden things. If they go first, they sneak and hide, not relying on speed and strength like The Big Guy. They are usually mobile, carrying little equipment. They rely on spotting danger first, stealth, reflexes and their wits to stay alive. They are often stealthy, but the focus can also be on choosing paths thought impossible, being inconspicious, or some other strategy.

In a fight, The Sneaky Guy will probably try to stay inconspicuous, looking for a weak spot to exploit or a way to confuse the enemy. Ranged weapons are common, as are daggers and short swords.

Many games, like Dungeons & Dragons, has prepared roles for The Sneaky Guy, like thief or rogue.

Related tropes are Stealth Expert, Technicolor Ninjas, Army Scout of the western movies, or the Scarily Competent Tracker. If a character manages to be both good at fieldcraft and fighting straight-up, it's usually a Ranger or the point man variety.

The Sneaky Guy corresponds to the thief in Fighter, Mage, Thief, just as The Big Guy corresponds to the fighter and The Smart Guy to the mage. Duos with a Big Guy are common. The Sneaky Guy can also easily serve as the Beauty in a Beauty, Brains, and Brawn trio, or The Chick in a group—at least they get to do more than as The Heart. In a Five-Man Band, The Lancer or The Smart Guy can double as The Sneaky Guy. If serving in The Squad, a not uncommon variation is serving as the point man, where The Sneaky Guy often takes on elements of the Big Guy.

Anime & Manga

 * In Rune Soldier Louie, which is basically set in a Dungeons & Dragons universe, Merrill is the lithe thief of the group.
 * Tsuchiya Kouta in Baka to Test to Shoukanjuu.

Comic Books

 * Nightcrawler in X-Men.
 * Glenn in The Walking Dead.

Films -- Live-Action

 * Malak is a cowardly thief who provides some comic relief in Conan the Destroyer.

Literature

 * Bilbo Baggins is hired for this very role by the dwarf party in The Hobbit, although he's himself initially unconvinced.
 * Benito Valdosta in the Heirs of Alexandria series.
 * Martinez in Norman Mailer's The Naked and The Dead.
 * Jame in Chronicles of the Kencyrath, especially in God Stalk, the first book.
 * Gray Mouser in Fritz Leiber's Lankhmar books.
 * In the Dragaera novels, Vlad's friend Kiera the Thief has a reputation as being able to steal anything and relies on stealth rather than combat prowess.
 * In the Redwall books, Martin the Warrior (who would be The Fighter) is best friends and partners with Gonff the Mousethief, who plays this role (there might be a Lankhmar allusion here).
 * Silk in the Belgariad.
 * Caius Blohm in David Drake's Redliners is a point man variation.
 * Ding Chavez in Tom Clancy's books, introduced in Clear and Present Danger, is another point man variation.

Tabletop Games

 * Most Rogue and Thief classes in RPGs.

Video Games

 * Fero in The Reconstruction.
 * The Spy class from Team Fortress 2.
 * Kasumi Goto in Mass Effect.
 * Ezio and Desmond of Assassin's Creed.

Web Comics

 * Haley in The Order of the Stick.