Young's memoir follows his failure to blend in after being given a job at Vanity Fair by legendary editor Graydon Carter. Young proves too crass and sarcastic for the pretentious world of big-time New York journalism. In adapting this story, screenwriter Peter Straughan changes Vanity Fair to Sharps, Toby Young becomes Sidney Young and Graydon Carter becomes Clayton Harding. Young is inhabited by Simon Pegg, which represents pitch-perfect casting since Pegg has a knack for being sympathetic and unsympathetic all in the same breath. As for Harding, Jeff Bridges delivers a scene-stealing performance that doesn't quite reach the level of Meryl Streep's tyrannical editor in The Devil Wears Prada, but that's only because Bridges isn't given nearly enough to work with.
In order to try and appeal to people who didn't read the book, Straughan misguidedly inserts too much slapstick humor and other gross-out gags. The film is at its best when Pegg and Bridges are on screen, but the supporting cast (Kirsten Dunst, Danny Huston, Megan Fox and Gillian Anderson) also delivers.
Film history is full of more than its share of serious journalists. If anything, its refreshing to watch How to Lose for a different take.
Cast: Simon Pegg, Kirsten Dunst, Megan Fox, Jeff Bridges, Gillian Anderson and Danny Huston
Director: Robert B Weide
Screenwriter: Peter Straughan
Producers: Elizabeth Karlsen and Stephen Woolley
Rating: R for language, some graphic nudity and brief drug material
Running time: 110 min.