"How to Lose Friends & Alienate People" is an ungainly title, difficult to remember and about as attractive as what it infers. If pressed to compare the film to something, one could call it a male version of "The Devil Wears Prada." Otherwise, the picture isn't one that is easily described, and not an ideal candidate for marketing folks trying to sell it to an audience. To say that the film is alternately ribald and adorable, cutthroat and illuminating, won't be enough to convince consumers to take a chance on the pleasures it has to offer, and that's a shame. This is a sparklingly handled comedy, not always free of clichés, but embracing of its occasional bad taste and respective softer side.

Growing up with a scholarly writer father and an actress mother, Sidney Young (Simon Pegg) has always yearned to be accepted into the Hollywood crowd. With a low-rent tabloid journalist job in London, however, the only way he's ever gotten close to fame and fortune is by sneaking into parties. When his go-getter work catches the eye of Clayton Harding (Jeff Bridges), editor in chief at New York City's celeb-minded Sharps Magazine, Sidney accepts the job invite and eagerly uproots himself to the Big Apple. At the bottom of the totem pole once more, the obnoxious-to-the-naked-eye Sidney has trouble fitting in with his coworkers—aspiring author Alison Olsen (Kirsten Dunst) is turned off by him before he's even started, running into her at a bar and refusing to take another seat to accommodate her boyfriend—and can't seem to gain much mileage with his story ideas and blatantly honest writing style. What Sidney does receive is a gateway pass into the world of movie stars, hotshot directors and domineering publicists—a place he's been forever obsessed with. Ultimately, he's not sure he likes what he sees.

A razor-edged exposé on celebrities and the publications that feed into them, "How to Lose Friends & Alienate People" is at times eye-opening, if not completely surprising, in its outsider's look at a Hollywood lifestyle that comes complete with a "yes" mentality and bosses who lord over the information that gets out about their clients in order to control their public image. Such is the case with flighty, dog-toting up-and-coming starlet Sophie Maes (Megan Fox), about to hit it big with the release of her new film, "Teresa: The Making of a Saint," and publicist Eleanor Johnson (Gillian Anderson), who only agrees to Sharps doing a story on Sophie if she has final say on what gets printed. Sidney is uncontrollably drawn to Sophie even as he sees her for the dim-bulb she is. When he proposes doing a truth-filled story on pretentious young filmmaker Vincent Lepak (Max Minghella) and receives the go-ahead, Sidney bashes out all of his feeling about a man who has the world at his fingertips and a knowledge of cinema that doesn't go back any further than Quentin Tarantino. Once read, Clayton Harding naturally tells him it's a no-go, leaving Sidney questioning whether he has what it takes to swallow his words and gain success through fluff pieces.

Director Robert Weide (TV's "Curb Your Enthusiasm") and first-time screenwriter Peter Straughan are not totally critical of the milieu they work within. When Sidney meets aging, all-but-forgotten actress Rachel Petkoff (Diana Kent) at a party and asks her for her autograph after prattling off all the movies and television he has loved her in over the years, her reaction is treated with an empathetic eye. Sidney has his moments such as this one, but he also suffers from foot-in-mouth disease, the censor to what comes out of his mouth turned off most of the time. It is this character trait that makes Sidney's actions very funny at the onset—meeting Thandie Newton for the first time and posing as a producer, he offers her a role in "Tits of Fury"—but also off-putting from a human relations standpoint.

Nonetheless, Sidney grows as the movie goes on, his flaws serving to uncover an admirable valiance. He is unapologetic in the things he believes in, and also encouraging and respectful to other people's dreams. It is because of this that Sidney starts to grow on Alison, her disdain for him turning to fondness as they spend more time together. The romantic subplot between these two is blessedly low-key, affecting, and sweet. For two characters who start off mixing about as well as oil and water, it is easy to see why Alison's view starts to change the more she gets to know about him. In return, Sidney is supportive of Alison's desire to be a novelist, a dream that has become a pipe dream in her eyes as she has allowed herself to be swallowed up by a job she has no passion in. A subplot involving Alison's oafish boyfriend, much-older editor Lawrence Maddox (Danny Huston), could have been done without—it's a given that he's not right for her—but it fortunately works itself out in an expedient fashion and only poses a brief threat to Sidney's feelings for her.

Coming off two star-making roles with director Edgar Wright (2004's "Shaun of the Dead" and 2007's "Hot Fuzz") and one less-esteemed followup without Wright (2008's "Run Fatboy Run"), Simon Pegg has now graduated to full-blown leading man status. Pegg is terrific as Sidney Young, getting big laughs early on with his stubborn, tell-it-like-it-is demeanor, and then developing nicely as a good-hearted, three-dimensional person. As Alison, Kirsten Dunst (2007's "Spider-Man 3") is radiant as usual, a game comic foil for Pegg and an ideal love interest with a story arc of her own. Dunst is especially astute in playing Alison's turmoil over where she has ended up in her life, a personal conflict that rings true. Supporting Pegg and Dunst are Jeff Bridges (2008's "Iron Man") as magazine bigwig Clayton Harding, who sees glimmers of his younger self in Sidney, and Megan Fox (2007's "Transformers"), doing an eerily dead-on, slow-drawled impression of Anna Nicole Smith as sexy actress Sophie Maes.

"How to Lose Friends & Alienate People" offers numerous tips on how to avoid just that. For one, don't cough up food on the back of a deceased magazine CEO's daughter, and two, definitely don't hide the body when you've accidentally killed a celebrity's beloved pooch. Silliness aside, "How to Lose Friends & Alienate People" is a smart, keen-eyed slice-of-life in addition to being a warmly realized love story. For viewers who can get past the turn-off of a title, they will find a film as entertaining and easy to like as it is shrewd about its subject matter.