Sensei for Scoundrels

"I look like you want to look, I fuck like you want to fuck, I am smart, capable and most importantly: I am free in every way that you are not."

—Tyler Durden, Fight Club

Are you a Chew Toy, A Woobie, a Dogged Nice Guy or just generally pathetic? Are women avoiding you like plague? Do you feel existentially lost in a cruel and uncaring universe?

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.

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.

Anime and Manga

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.
- *cough* Names to Run Away From Really Fast *cough*

Comic Books

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.

Film

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.
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 Alter Ego in The Mask, depending on the adaptation.

Literature

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.
Yunior from The Brief Wondrous Life of Oscar Wao tries to be this to Oscar, but fails miserably.
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.
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.

Live Action TV

Parodied in The Fast Show 's Swiss Toni.
Barney really wants to be this to Ted on How I Met Your Mother. Ted rarely listens.
Russell acts as one to an Amish boy on his Rumspringa in the Rules of Engagement episode "Twice".
Tully is this to George on Being Human (UK), but with added Ho Yay and Squick.
The CSI: Miami episode "The Score" featured a man who ran classes on how to pick up women.
Sam Adama from Caprica is this to his nephew Willie Adama.

Web Comics

The perfectly-respectable variant is used in 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. Gunnner didn't take it very well.

Web Original

This episode^{[dead link]} of Wainy Days, which demolishes real-life pickup artist "Mystery" with a knock-off played by Paul Rudd.

Western Animation

A Pimp Named Slickback from The Boondocks probably counts.
Parodied in Venture Bros. by the character Henry Killinger

Real Life

Mystery and Neil Strauss built their real life careers on this sort of thing. (See Literature.)
Tucker Max, despite despite every single thing he's ever said or done, is seen as this by both his Fan Dumb and his Hatedom.