Loser takes it all

  • The List
  • 2 October 2008
Loser takes it all

Saul Levi meditates on the loser arts

To understand the real art of being a loser, we need a definition. This one from the 2008 Oxford Pocket Dictionary of Current English will do: Los•er (noun): (informal) a person who fails frequently or is generally unsuccessful in life: a ragtag community of rejects and losers.

So, we shall take our lead from this informal definition, for it is from this rocky ground that fertile shoots spring.

Toby Young’s cringingly funny 2002 book How to Lose Friends & Alienate People (and the subsequent film) are only the most recent of a cultural catalogue defined by the nobility (or complete lack of it) of failure.

Young’s book took its name from Irving D Tressler’s hilarious and bestselling literary spoof of Dale Carnegie’s dreary proto-capitalist self help text How to Win Friends & Influence People. Carnegie’s book, originally published in 1936, had its highest sales as the US economy segued from postwar depression into the regimented rewards of the Jet Age, when Japan was the only nation to rival the growth and revival of the United States. Japan had its own history of mad, tragic heroes, ranging from Prince Arima, whose death climaxed in a court intrigue to rival Hamlet’s, to the kamikaze pilots of WWII. Heroes or villains, losers or winners? Are they not just two sides of the same coin depending on your nationality, religious beliefs and one’s sense of societal obligation?

Political and cultural ambiguity across all the arts has allowed us to welcome some examples of the reactionary loser into our hearts. Think of 24’s vigilante secret agent Jack Bauer played by Keifer Sutherland, De Niro’s Travis Bickle from Taxi Driver or Danny De Vito and Richard Dreyfuss’ feuding salesmen in Barry Levinson’s 1987 comedy film, Tin Men. The mental anguish and moral dilemmas of these characters are rooted in the meditations of Rodion Romanovich Raskolnikov, protagonist of Fyodor Dostoevsky’s novel Crime and Punishment, whose violent actions both free him and imprison him.

Ultimately it’s all so much semantics. The only way to really celebrate the life, work and stories (comical or otherwise) of the fallen, those touched by madness, sadness or just ill fortune is to indulge and never look back at the folk in the big house. Nowhere is that more skillfully illustrated in those who make it their business to be losers. Some of the most vivid and skilled portrayals are in the 70s and 80s films of Woody Allen. Similarly, Sam Peckinpah’s Bring Me the Head of Alfredo Garcia, and even Kathryn Bigelow’s sci-fi yarn Strange Days, a film which predicted the microwaveable malaise of Second Life.

Elsewhere, few have indulged the lifestyle (in notion at least) more than Tom Waits, the first decades of whose career drew almost exclusively from the barfly’s book of etiquette. See also undeground rock doyens Mark Lanegan and Greg Dulli: they don’t call themselves The Gutter Twins for nothing. The daddy of them all, however, is Charles Bukowski, whose Ham on Rye could be the loser rule guide book.

The final category, the naïve loser, includes those who know no better and whose back luck, bad choices, or in the case of Napoleon Dynamite, bad breeding, cause them to be the butt of everyone’s jokes. See also endearing Kiwi comedy duo Flight of the Conchords.

So political, methodical or just plain unintentional, indulging the loser is a path to creative righteousness. Just don’t count on that path being paved with gold any time soon.

Less is more

Mark Robertson and Hamish Brown drag up some of the definitive works of loser art and discover some true genius

Down and Out in Paris and London

George Orwell was ‘method writing’ long before any of the Hollywood sprats took up ‘method acting’. Not enough to wonder what it is like to live below the bread line, sleeping on benches and washing dishes for change, Orwell lived it. Bloody good read, mind.


Without even an Xbox or Facebook to distract him, this youthful, melancholic loser set the gold standard by which all Napoleon Dynamites are compared. Should have got his finger out and bumped off his uncle/stepdad when he had the chance rather than sitting about the castle procrastinating all day.

Steven Wright

Known to some as the deadpan radio DJ in Resevoir Dogs, Wright is better regarded as the American master of the self-depreciating one-liner. The clown hair and hangdog expression were made to absorb the crushing lows of lfe. As he so deftly put it: ‘You can’t have everything – where would you put it?’

Some Mother’s Do ‘Ave ‘Em

Ah, Frank Spencer, a man who, despite the ample opportunities offered by 1970s Britain, seemed unable to manage lunch never mind hold down a job. Why Betty stayed with him remains a mystery.
Blues music That’s right, all of it. Every last note. Hard luck stories don’t come more, er, hard than a blind man with a 60 cent guitar and a dead dog. That the music has been reappropriated by anodyne, ageing hipsters like Eric Clapton suggests a very different kind of loser altogether.


The 2004 comedy takes the social ineptitude of Spencer to the wine Valleys of California in the form of Miles, an effete snob who is very lovable, mostly because of his steadfast resistance to good fortune. Obsessive to the point of self-destruction, he gets the fine wine and even finer gal but still messes it up.

The Simpsons

Matt Groening may be able to make coffee tables out of stacks of his spare $100 bills these days, but his bitter, bitterly funny take on suburban America was born out of painful experience as a loser drone. The holy trinity of loserdom: Moe, Barney and Homer, remain the benchmark by which all animated losers – Wile E Coyote, Foghorn Leghorn, Tom from Tom and Jerry and Peter Griffin – must be measured.

How to Lose Friends and Alienate People

  • 3 stars
  • 2008
  • US
  • 1h 50min
  • 15
  • Directed by: Robert B Weide
  • Written by: Peter Straughan, Toby Young (memoir)
  • Cast: Simon Pegg, Kirsten Dunst, Megan Fox, Danny Huston, Gillian Anderson, Jeff Bridges, Brian Austin Green

Toby Young's semi-scandalous memoir about the period the gobby English journo spent carousing with the rich and famous while working at a glossy magazine in New York is given a mainstream movie makeover with this enjoyable enough romantic comedy. Young's rudely confessional and frequently very funny observations are now…