Freddie Simmons

An author who turned failure into success

Arty Types

This article is taken from the March 2023 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issues for just £10.

Freddie Simmons published his first volume of memoirs at the early age of 39. Last in the Sack Race, a wry and self-deprecatingly humorous account of his misadventures at school, was widely and favourably reviewed, not least by old friends now at large in the world of journalism. 

“Mr Simmons,” a man who had once shared a study with him at Charterhouse informed readers of the Observer, “has brought off the by no means easy feat of making a success out of failure.”

Three years later a second instalment followed. You Found Three Questions You Could Answer? (words supposedly addressed to Freddie by his tutor after his first finals exam) took in such embarrassments as the double third in English Literature he acquired from King’s College, Cambridge and the job interview in which he was unable to remember the name of the prestigious accountancy firm to which he was applying.

All this was twelve years ago. Since that time there have been three more volumes: Bringing Up the Rear, which covered his early experience of paid employment and ended with his sacking from the advertising agency for being found drunk under the boardroom table; All at Sea (a disastrous interlude spent working for the publicity department of P&O); and Not Quite Our Kind of Person, an affecting, yet still self-deprecatingly humorous summary of his brief first marriage to a minor aristocrat into whose family he signally failed to fit.

Each book has sold several thousand copies

Each book has sold several thousand copies. Their effect has been to make Freddie, now in his middle fifties, a regular guest on chat shows and a practised supplier of wry and self-deprecatingly humorous essays to Sunday newspapers.

Yet the suspicion (at any rate among Freddie’s admirers) that National Treasuredom cannot be far off is balanced by an awareness of the very considerable gap, between his public persona and the almost mythical figure who marauds through his books.

However bumbling, useless and complacent he is on the page, Freddie, when brought to a literary festival stage or The One Show, turns out to be unexpectedly sensitive. He is keen not to be reminded of the time he accidentally knocked out one of the umpires whilst playing cricket for the Captain Scott Invitation XI or mistook a bowl of pot-pourri in the Ernst & Young partners’ dining room for a pre-lunch snack. 

Old friends eager to play up to the image Freddie has created for himself are more often than not rebuffed, and he is supposed to have left last year’s school old boys’ dinner in tears.

It is all very odd. As a Radio 4 producer who invited him onto a comedy panel show with the aim of “having a laugh” and was rewarded by half-an-hour’s polite stonewalling once put it: “People who spend their lives telling everyone they’re an idiot shouldn’t be surprised if they get treated like one.” As for the immediate future, just last week Freddie’s agent was surprised to receive a proposal for a book on the history of Palestine.

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