‘How to Lose Friends and Alienate People’ movie review: dour Simon Pegg comedy

An unfortunate title that describes its contents all-too-well, Robert B. Weide’s How to Lose Friends & Alienate People does just that, delivering a piece of cinema just as unlikable as its leading man. 

I haven’t read Toby Young’s autobiographical memoir on which the film is based, but I sincerely doubt that a) it took the structure of your average Hollywood romantic comedy, or b) he presented himself as this big of an ass.

Toby Young started the “low culture for highbrows” mag Modern Review in the UK in the early 90’s before coming to NYC to work for Vanity Fair

He failed – quite spectacularly – during a three year stint there, which included hiring a stripper for the office on ‘bring your daughter to work’ day; but he turned his failures into How to Lose Friends and Alienate People, the bestselling novel that has “inspired” this feature film (a second novel, The Sound of No Hands Clapping, took inspiration from Young’s failure as a Hollywood scribe.)

In this film version of How to Lose Friends, Simon Pegg stars as a Sidney Young, who leaves Post-Modern Review in the UK to work for Sharps magazine in New York under hotshot editor Clayton Harding (Jeff Bridges). 

There he alienates people (I don’t think he had any friends to lose) while competing with office superior Lawrence Maddox (Danny Huston) and lusting after rising starlet Sophie Maes (Megan Fox), though he somehow manages to endear himself to coworker Alison Olsen (Kirsten Dunst).

Young’s story in itself is half-compelling, but the film mostly ignores it while travelling the well-worn roads of lowbrow comedy and storybook romance, the latter of which is screenwriting 101 material: boy lusts after beauty, realizes he really loves his close friend, by which time he’s lost her and has to win her back. 

The cliché stuff completely undermines Young’s story, and to top it off, none of it is all that funny; best bit: a fake trailer for a Mother Teresa biopic starring Maes.

Pegg is a likable actor, and the deadpan persona and wit he displayed working with Edgar Wright could have been enough to alienate the other characters and still endear him to the audience. 

But no, he’s a pratfalling caricature here, stumbling over himself drunk, wrestling starlets at awards ceremonies, pushing his character past any potential empathy. 

Which is all fine until we’re asked to accept him as a romantic lead; by all means, we want this creature kept as far away from Kirsten Dunst as possible. 

I was reminded of David Spade lusting after Sophie Marceau or French Stewart matched with Bridgette Wilson in a pair of misguided 1999 comedies, Lost & Found and Love Stinks; the memories weren’t pleasant.

The rest of the cast is, by and large, wasted; most disappointingly, Bridges and Huston, along with Gillian Anderson as a press agent. Fox is beautiful here but her character is insultingly underwritten.

A disappointment from director Weide, coming off TV’s Curb Your Enthusiasm and the excellent 1998 doc Lenny Bruce: Swear to Tell the Truth.


Jason Pirodsky

Jason Pirodsky

Jason Pirodsky has been writing about the Prague film scene and reviewing films in print and online media since 2005. A member of the Online Film Critics Society, you can also catch his musings on life in Prague at expats.cz and tips on mindfulness sourced from ancient principles at MaArtial.com.

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