Richard Branson's Bad Idea Jamboree

Sir Richard Branson, the man who, more than any other, sums up the phrase "lower the retirement age now", is unhappy. His own Virgin Trains have lost their long-time rail franchise.

Richard would like us all to believe that he should remain in charge of the trains that run through the northwest of England, because he is the best person in the universe at running things. It's a myth he's spent years carefully cultivating, but it remains balls. Virgin Clothing, Virgin Flowers, Virgin Games, Virgin Cars, Virgin Dog Turd In A Radioactive Box – all have crashed and burned in their time. And that's not even the start of it.

Back when the Zune was still a twinkle in the eye of a man who has since been sacked and frogmarched by security off of Microsoft's Seattle Campus, Virgin decided to take on iTunes. Smart move, right? Jobs and Branson going head to head to figure out who was the best dropout corporate renegade who made nerdy business studies undergrads with suspiciously over-developed career plans weak at the knees.

Except that Virgin's version of the iPod was a hunk of junk that had already missed the curve, and rather than plough in the sort of deep investment that it would take to compete with Apple, they had simply re-badged a blob of silver plastic, given it a paltry 128MB of storage and no LCD screen, and tacked on a music store – Virgin Digital – that opened in 2006, and then closed without warning two years later.

Failed because: It wasn't even as good as the Zune.

Suggested remedy: Sack everyone who told you to compete in this market, then hire them again so you can sack them again.

Crapometer: 4/10

That name. It was probably worth a slight titter in 1978. Hell, it was probably worth a wry smile in the early months of 1979. But if you started a company tomorrow and called it Speculum, you wouldn't presume to later brand that onto perfume, would you? Virgin Brides just made everyone think of hymens and whether white would be a suitable colour for your big day, given what you did with Jon in the ASDA carpark after the Eclipse '03 NYE Party.

For brides to be, the toss-up was always: Would the waking nightmare of having a Virgin-branded wedding and bridal gown be compensated by a cost saving estimated to be somewhere in the tens of pounds? Branson shaved his beard and wore a wedding dress in order to launch it. If you wanted to shave your beard and wear a wedding dress, you should have just done it, pal. You've got nothing left to prove, and no one likes you anyway.

Failed because: Richard Branson shaved off his beard and wore a wedding dress. Suggested remedy: To avoid awkward virginity questions, should have been marketed towards child-brides instead.

Crapometer: 5/10

Richard Branson approached his job of marketing Virgin Cola like a rhino approaches mating season. He went into a lather of stunts. He drove a tank into Times Square. He brought out a bottle in the shape of Pamela Anderson. He rode around Golders Green in an armoured car giving the sieg heil and eating a baby's roasted leg still in its little bootie. Except not that. But the chief probem with Virgin Cola, as anyone who remembers it will attest, wasn't marketing. It was that it tasted like dead cat. A nuttiness. An inexcusable fruitiness. A sense of food scientists running around trying to figure out what Coca-Cola's mystery ingredient 7X was, and deciding it must be cloves and anchovies. It was so bad you were often better off with the Tesco Value stuff. And they thought 7X was weevils and urinal cake.

Failed because: People thought he was joking.

Suggested remedy: Raise eyebrows more sharply when joking.

Crapometer: 6/10

Coca-Cola does what it does quite well. There are screw-ups, sure. But in spite of Cherry Coke, New Coke and Wayne Rooney Coke, it has yet to develop its own brand of wine. This is not a mistake. The Coca-Cola Company didn't fail to spot the key marketing overlap between selling sweet, sugary gut-rot piss and appealing to people looking for a reasonable bottle of cabernet. Richard Branson, however, during his drinks phase, seemed to see these phantom opportunities around every bend.

Virgin Vines offered discerning drinkers nothing. It didn't even offer undiscerning ones anything, because as anyone who has hung round the booze aisles for more than five minutes will know, the whole point of cheap wines is that you put fancy labels on them so they look like they're from a tiny town in the Languedoc with three hundred years of family vintner tradition (rather than mixed by hydraulic steel arms in swimming pool-sized vats on an industrial estate outside Lyon), and then you "discount" them from eight quid to five. “Virgin Vines believes wine should be all about having fun and loving the taste… not waxing poetically about meaningless wine-speak and food pairings," ran the bumpf. The ad slogan was "Unscrew it, let's do it.” The chief copywriter has since shot himself.

His booze hounding didn't end there. There was Virgin Vodka. Virgin Energy Shot, a failed attempt to work the Red Bull dollar. Virgin Tequila. And Virgin Ooze – Dickie's attempt to compete with Smirnoff Ice. The latter was “a happy blend of bubbles and red berries infused with 5.6 percent alcohol”, a phrase that evokes a shoeless woman pissing in the doorway of a provinical branch of Dixon's, no matter how you inflect it.

Failed because: Branson was a secret dipsomaniac.

Suggested remedy: 1) Acknowledge powerlessness over alcohol. 2) Accept a higher power. 3.) The rest of the steps.

Crapometer: 9/10, 4/10, 4/10, 7/10, respectively.

In 2003, Virgin decided to open 30 women's underwear shops across the country. Because when you are choosing what to drape across your most intimate area, the first thing that flits to mind should be 91 peroxided teeth and an off-ginger maw of facial hair.

That wasn't their slogan, but the public certainly saw it like that. Things went so badly that Virginware ended up in a fire-sale situation: across the country, 30,000 pairs of knickers and bras going cheap-cheap-cheap as their stores were liquidated. There are probably still thrifty types out there who bought 40 pairs for 70 quid back in 2005, and now use them up at the rate of five a year. A bargain, so long as you never have sex with anyone. Ever.

Failed because: Richard Branson is erotic anthrax.

Suggested remedy: How about starting with a name that doesn't resemble Tupperware and working your way up from there?

Crapometer: 8/10

Follow Gavin on Twitter: @hurtgavinhaynes