The Sensei for Scoundrels might be the answer to your prayers. He is everything you wish you could be as a man: strong, attractive, fearless and a huge success with women. Of course, he's also probably deeply disturbed, and possibly very evil. You may find him at the Thug Dojo, but a School of Hard Knocks is more likely.
The main character winds up following The Sensei for Scoundrels in the hopes of becoming the kind of man he always wanted to be. In a Lighter and Softer story, the main character will very often end up rejecting the sensei's advice by the end and win the girl on his own terms. In Darker and Edgier works, the hero very often ends up becoming as bad as the mentor and loses all of his positive characteristics in the process.
Of course, it's also possible the mentor is perfectly respectable and our protagonist will end up better for the experience.
These guys also exist in real life, though they're usually not quite as psycho and probably are financially motivated.
Compare and Contrast the Big Brother Mentor whose relationship with the protagonist is a bit more friendly and has fewer unfortunate drawbacks. There's a certain amount of overlap with the Manic Pixie Dream Girl, considering both are slightly unhinged characters who encourage a tightly-wound protagonist to relax and have a little more fun in his miserable life.
See also Evil Mentor.
- Bleach Bount arc. Maki Ichinose left the Soul Society in despair after his Captain was killed. While wandering he was almost killed by a hollow but was saved by Jin Kariya. Ichinose swore to follow Kariya and help him defeat the Soul Society. He eventually learned that Kariya planned to destroy the entire Soul Society and turned on him.
- Kensei Ma and Sakaki Shio of Kenichi: The Mightiest Disciple. Their training methods often involve perversion and getting drunk, respectively.
- Jack Rakan of Mahou Sensei Negima!. He might be smart, but he's definitely crazy and perverted, to the point that they only techniques he doesn't make up on the spot are the ones used to harass females. Of course, Negi specifically begins training with him because he wants to learn how to be more of an idiot.
- Considering how many girls are already tripping over each other just to be near Negi, he doesn't need the help.
- The Hentai anime The God of Groping.
- Kozue Takanashi does this for Yachiyo Todoroki in WORKING!! - Yachiyo is looking for advice on what she should do to get ready to hang out with a male co-worker, without any designs on romance. Kozue, a Hard-Drinking Party Girl who isn't shy about, well, anything, basically gives advice on how to get laid. Most of it flies over Yachiyo's head, though what doesn't manages to be useful.
- Subverted in Green Arrow during DC Comics Missing Year when, feeling he's gone soft, he hires a literal sensi for Scoundrels to teach him and his family to fight dirty. He becomes a Sink-or-Swim Mentor when he recruits his former student to give Green Arrow a trial by fire.
- Taskmaster is a literal, for-hire version of this trope, providing combat training to Mooks and aspiring Super-Villains.
- Tyler Durden from Fight Club. See literature for more information.
- Frank T.J. Mackey from Magnolia, is definitely one of these, though we don't learn much about any of his students. His famous mantra is "Respect the cock and tame the cunt."
- Dr. P from School For Scoundrels is also this kind of guy.
- The titular Roger of Roger Dodger.
- Trent and Sue from Swingers.
- Robert Morse's character to Walter Matthau's in A Guide For The Married Man.
- Will Ferrell's part in Wedding Crashers.
- Talby in Day of Anger. He takes Scott, the much-abused young hero, on as a sidekick and turns him into a gunslinger; it takes Scott most of the movie to realise that his mentor is evil.
- Changing Lanes: Gavin's father-in-law and senior partner, Stephen Delano (played by Sydney Pollak.) Part of Gavin's Character Development throughout the film is his realization that Delano is grooming him to become an Amoral Attorney, while getting Gavin to do the majority of the firm's dirty work.
- Stanley Ipkiss' unrestrained Superpowered Alter Ego in The Mask, depending on the adaptation.
- Peter Cook's Satan is this to Dudley Moore's hapless Everyman Stanley, in Bedazzled (1967), where he offers the standard Eternal Soul contract to a guy hungry for the love of a particular woman.
- Cedar Rapids: Dean Ziegler, a hard-drinking, foul-mouthed Jerk with a Heart of Gold, to Tim Lippe. Tim does his best to reject Dean's tutelage, only to learn that despite his flaws, Dean's a stand-up guy who does right by his friends (and that most of Tim's other "friends" don't).
- Yunior from The Brief Wondrous Life of Oscar Wao tries to be this to Oscar, but fails miserably.
- This trope was initially named for Tyler Durden in Fight Club, who teaches the nameless protagonist to stop being so emasculated and to go Fight Clubbing as well as some other... matters.
- Tyler is an especially interesting example of this trope, as he's not actually a real person, but rather a wish-fulfilling, disassociated identity of the protagonist that does all of the things the protagonist wishes he could do.
- The Game is based off of Neil Strauss attending seminars on how to become a pickup artist. He eventually became one of the teachers himself.
- This features in the plot of Macho Man (German title) by Moritz Netenjakob. Daniel, the protagonist, has no success with women because he is "too soft" to be taken seriously as a potential boyfriend. When he meets Aylin, who is a very attractive Turkish entertainer at the hotel where he's staying, he is very surprised that she is attracted to him. They start dating and he discovers that Turkish culture values different gender roles and a more "dominant" kind of masculinity. He learns to fit in due to the influence of Turkish men. This leads to his breakup with Aylin since she was originally attracted to his softness and non-macho behaviour. But he apologizes by singing the Smurf song to her and thus regaining his softer image.
- Dean Moriarty in On the Road is the first type, where the narrator eventually becomes disillusioned with this character. The ending portrays Dean as actually being rather pathetic.
- Lord Henry to the titular character in The Picture of Dorian Gray. It ends badly.
- Angel: Illyria can't believe Angel is wangsting over being the head of a multi-billion dollar conglomerate. She sets him straight with this speech.
Illyria: So much power here! And you quibble at its price. If you want to win a war, you must serve no master but your own ambition.
- Tully is this to George on Being Human, but with added Ho Yay and Squick.
- Sam Adama from Caprica is this to his nephew Willie Adama.
- Jordan Chase in the 5th season of Dexter is the evil version of this trope.
- The CSI: Miami episode "The Score" featured a man who ran classes on how to pick up women.
- Parodied in The Fast Show 's Swiss Toni.
- Barney especially wants to be this to Ted on How I Met Your Mother, although Ted rarely listens. In general though Barney will take any opportunity to be this to anyone, such as Randy in season 3, or the two guys he meets on the side of the road in season 9.
- Russell acts as one to an Amish boy on his Rumspringa in the Rules of Engagement episode "Twice".
- Star Trek: Deep Space Nine: Garak. More than once, he responds to an idealistic character being suspicious of him with, "You're learning," or, "There may be hope for you yet," to the point where the latter is almost a catch-phrase for him.
- An unintentional example in Cobra Kai: Johnny Lawrence grows up into one, reforming Cobra Kai's image but teaching his new students how to fight with pragmatic methods. unfortunately, he doesn't reform the underlying philosophy, and his students turn into the same types of bullies that they sought to deal with.
- In Final Fantasy Brave Exvius, Jake attempts to take this role with Rain, when the latter is confused by Dark Fina's Tsundere-like reactions, due to the fact that Rain is Oblivious to Love. Jake, a Casanova Wannabe to a ludicrous extent, attempts to give Rain advice on how to resolve the issue in perhaps the most perverted way possible - to the extent that another party member dashes in to prevent him from giving any further advice - feet first, into Jake's torso.
- The perfectly-respectable variant is used in The Order of the Stick preceding Elan's literal level in badass. The mentor in question is named Julio Scoundrél.
- In Zap!, Gunner Strife tried to be one of these to Zap while training him in the use of psychic powers. It worked up until Gunner told him to use his psychic powers to make Leona fall in love with him. Zap decided to block Gunner from telepathically contacting him instead. Gunner didn't take it very well.
- Sam Starfall decides to take this role to Florence in Freefall, although by his scavenger species' Blue and Orange Morality, this is simply being a good mentor. Prior to the comic starting, he had also provided similar education to Robot Buddy Helix.
Chief: Breaking and entry. Unauthorised access to cyber assets. Assault. Theft. Trespassing.
Sam: She was law-abiding before she met me. Am I a good teacher or what?
- This episode of Wainy Days, which demolishes real-life pickup artist "Mystery" with a knock-off played by Paul Rudd.
- The SCP Foundation: SCP-3512 features a pick-up artist's guide written by such an individual, which takes a sharp turn for the arcane and the unhinged from the twelfth chapter onward. Following its instructions does strange things to you, and worse to the women you try its teachings out on.
- A Pimp Named Slickback from The Boondocks is this in his second appearance, in which he teaches Tom to stand up to his wife (who he suspects of being unfaithful with Usher). It backfires and Hilarity Ensues.
- Parodied in Venture Bros. by the character Henry Killinger
- Hondo sees himself as this in Star Wars Rebels.
Hondo: Wait, wait! Does this mean I am not getting my finder's fee?
Ezra: You never were.
Hondo: Perfect answer. I am So Proud of You right now. I never had a student learn this quickly.