• A Warholesque treatment of Bob Skinstad, left, hangs in the foyer of Ten Bompas. Pictures: SUPPLIED

  • A painting of Amy Winehouse by Joanna Flatau at Ten Bompas. Pictures: SUPPLIED

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WHAT do Amy Winehouse and Bob Skinstad have in common? Not much, you’d think. Skinstad is alive and thriving, a successful athlete-turned-entrepreneur, his rugby career a pleasant memory and the foundation for days filled with outdoor leisure pursuits; Winehouse’s death by alcohol poisoning in 2011 hardly came as a surprise after years of substance abuse and mental illness that overshadowed her musical talents.

They do, however, share at least one thing: both are represented in the art collection of Christoff van Staden and Peter Aucamp, the owners of Ten Bompas in Johannesburg. In the foyer of this boutique hotel hangs a triptych in which portraits of a young Skinstad are given the Andy Warhol treatment — green hair and pink lips playfully emphasising the poster-boy good looks that seemed to contribute to his popularity as much as his skill, speed, and strength on the field.

Marilyn-Bobby is looking away into the middle distance, but if he could just turn his head slightly to the left, he might catch the eye of Ms Winehouse, whose image adorns a wall in the hotel’s restaurant bearing her surname. It’s an impressionist rendering of the sexily scraggy singer, her wispy frame criss-crossed by streaks of red and black that give the suggestion of a dishevelled outfit and echo her pursed scarlet lips (from which, inevitably, a cigarette dangles) and her ebony hair.

Polish-born artist Joanna Flatau has given her subject haunting azure eyes. An allusion to Winehouse’s place in the pantheon of "blue-eyed soul", perhaps? Yet, they have a lifeless gloss, like sunglasses. Visually, the painting lends a certain edginess to the otherwise tranquil, upmarket atmosphere of the restaurant.

Staring up at Amy as I dined there earlier this week, I was acutely aware of the feminised Bob Skinstad I had encountered on my arrival at Ten Bompas. There was something about this odd couple that merited further speculation. They went together like the wine and food pairings that executive chef Johannes de Bruijn and his team had prepared: at first they seemed to clash, but soon they became perfectly complementary. Or so, I told myself as I drank a glass of Thelema’s Verdelho while my palate lit up with a starter of barramundi and black rice risotto.

And then, somewhere between the roast lamb main course and the Crottin cheese for dessert, I realised something else about Bob Skinstad and Amy Winehouse: I didn’t like either of them very much when they burst onto their respective scenes.

Skinstad struck me as a little cocksure — his dazzling performances on the rugby field commanded respect, but all that tongue-lolling annoyed me. He was having too much fun; it all came too easily to him.

And he played for the Stormers.

Winehouse, for her part, had an astounding voice and a songwriter’s gift, but seemed, to put it bluntly, trashy. She came across as a caricature: swaggering, swearing, boozy, loutish, high, crass.

Yet in both cases, a traumatic event broke the spell cast by celebrity coverage in the media — a series of misrepresentations that I had consumed uncritically. Winehouse’s untimely death forced me to see her sympathetically, as a feeling fellow human; her suffering, her creativity, her unhealthy relationships, her flair, these were all irresolvable aspects of a complex, troubled, brilliant individual.

It made me revisit her music with newly appreciative ears.

Skinstad’s "trauma" was hardly comparable — a severe knee injury following a car crash — but it also changed the way I saw him. His became a story of setbacks and comebacks, of patience and perseverance that earned him a position in the 2007 World Cup-winning squad (and, of course, a few years prior to that a brief stint at the Lions). I looked again at Bobby of the late 1990s and I actually liked what I saw.

Recalling these changes of heart, I wondered how many of my current views and attitudes I’ll find myself disagreeing with in years to come. There’s a lesson in there somewhere. Call it "the Winehouse revelation" if you will.