Toby Young's book "How to Lose Friends & Alienate People" is one of the most annoying memoirs of all time. It makes sense, of course. If Young could lose friends and alienate people so easily, he'd have to lose and alienate his readers. A paradox sure, but appropriate. Just as fitting would be a movie adaptation that isn't enjoyable to watch. The guy playing Young should be so despicable that he's not even worth watching. He couldn't be like Billy Bob Thornton's amusing curmudgeon type of character. He'd have to be annoying enough to want to throw things at the screen and walk out. At least the movie version, which doesn't come out until next fall, co-stars one of the most irritating actresses, Kirsten Dunst.

Otherwise, though, How to Lose Friends & Alienate People looks too funny. Just look at this new trailer, courtesy of The Sun. First of all, it's impossible for me to hate Simon Pegg. Even less hate-worthy than Billy Bob Thornton's curmudgeons, Pegg is actually one of the most lovable annoying guys ever to grace the screen. He's an enjoyable bad boyfriend, an enjoyable bride-ditcher, an enjoyable pretentious co-worker, etc. Even though the trailer makes How to Lose look like a Ben Stiller comedy, Pegg still makes it seem funnier than that somehow. In addition to starring Pegg, it probably helps the movie's appeal that it's directed by Robert B. Weide, who has a lot of experience with uncomfortably (yet hilariously) offensive people from directing multiple episodes of Curb Your Enthusiasm and the Oscar-nominated documentary Lenny Bruce: Swear to Tell the Truth. It also helps that the trailer doesn't show much of Dunst.

[via Empire]

I keep wondering if I will like the movie version of Toby Young's memoir How to Lose Friends & Alienate People. I hated the book, mostly because I couldn't stand Young's pathetic voice, but so far the casting of the adaptation has me intrigued. With the exception of Kirsten Dunst, the players are of a high enough caliber to make all the unlikeable characters at least enjoyable to watch -- especially now that the great Jeff Bridges has signed on to play the character based on Vanity Fair editor Graydon Carter (named Clayton Harding in the script). Also added to the cast is Gillian Anderson, who will play a top PR person. Bridges and Anderson join Dunst, Danny Huston and Simon Pegg, who will star as Young.

The casting of Bridges as Carter should make How to Lose Friends even more comparable to The Devil Wears Prada, but I hope the actor won't make his character as much of a caricature as Meryl Streep made hers -- though I don't mean to put Streep's Oscar-nominated performance down. I would just rather Bridges play a more complex, believable person, who could be completely understood as the villain in Young's miserable world, while also appearing to audiences as a smart, justifiably difficult boss. After all, the book suggests that -- unlike Andy's resentment of Miranda in Prada -- Young actually has a lot of admiration for Carter. And more than Carter, the other Condé Nasties or anyone else, Young is his own villain.

In addition to the casting, I am anxious to see what the tone of How to Lose Friends will be. Directed by Robert B. Weide, who is an enormous fan and documenter of the work of Kurt Vonnegut, Lenny Bruce and the Marx Brothers, as well as a former director for Curb Your Enthusiasm, the movie will hopefully be influenced by the humor of at least one of those subjects. I also hope that the movie is good enough to get Weide some more clout in Hollywood. For ten years I've been dying for him to get to work on a project he once mentioned interest in: an adaptation of Vonnegut's The Sirens of Titan. How to Lose Friends & Alienate People begins shooting next month.