Set against the bright lights of Manhattan, a tale which takes a comic, urbane look at the modern male ego at war in the singles scene trenches. Roger Swanson is a hopelessly cynical advertising copywriter with a razor-sharp wit who believes he has mastered the art of manipulating women. But Roger's seemingly foolproof world of smooth talk and casual sex begins to unravel when he is paid a surprise visit by his teenager nephew, Nick. Hoping to settle, once and for all, the issue of his virginity, Nick begs Roger to school him in the art of seducing women. Welcoming the challenge, Roger guides Nick through the city's wild nightlife for an all-night crash course, only to realize that he--the adult--still has something to learn about what women, and men, really want.
Written by Sujit R. Varma

All right, fine.

There have already been three movies which have dealt with this topic. One of them was unreleased, one flew into the cinema and flew out and the last one was a critical and financial hit. All three films lacked quality and could have done considerably better considering the topic area.

There was one other film, Magnolia, but this dealt with Tom Cruise's issues with his father more than his character's understanding of the female mind.

Written by Sujit R. Varma

That's the same guy who wrote Let The Game Begin...

I posted it not so much on the pick up part but rather his 'seemingly good understanding' (he nails their situations accuratly, kinda like californication with meredith ^^) of women (or at least he's good to make them angry )

Tom Cruise/Magnolia was nominated for Golden Globes,

There is controversy over the idea that Cruise's character is based off of Ross Jeffries. Cruise denies that this was the case.

Given the performance, I am more likely to believe him. Cruise's character is nothing like Ross Jeffries. If anything it is much, much closer to Tyler from RSD.

According to Neil Strauss in "The Game", Ross Jeffries claims that the character Frank T.J. Mackey (played by Tom Cruise) in the film Magnolia, who gives seduction seminars, is modeled after Ross Jeffries. Cruise vehemently denies this, citing hours of character development that did not once mention Jeffries.[9] Though, according to Neil Strauss in "The Game", the film's director did mention Jeffries as one of the influences when writing it.

Cruise was interested but nervous about the role. They met with Cruise along with De Luca who helped convince the actor to do the film.[3] Frank T.J. Mackey, the character that Cruise would play in the film, was based in part on an audio-recording done in an engineering class taught by a friend that was given to Anderson.[2] It consisted of two men, "talking all this trash" about women and quoting a man named Ross Jeffries, who was teaching a new version of the Eric Weber course, "How to Pick Up Women," but utilizing hypnotism and subliminal language techniques.[2] Anderson transcribed the tape and did a reading with Reilly and Chris Penn.[3] The director then incorporated this dialogue and his research on Jeffries and other self-help gurus into Mackey and his sex seminar.[2]