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Justin Bieber performs at the 40th Anniversary American Music Awards on Sunday, Nov. 18, 2012, in Los Angeles. Bieber will perform at the Grey Cup halftime show Sunday.AP - John Shearer/Invision/The Canadian Press

When we look back at career of Justin Bieber – be it in five years or 50 – there is a fair enough chance we will see this moment in time as his awkward stage. Awkward stage at best, that is. At worst, this is the beginning of the end.

His weird autumn, which concludes today with a half-time appearance at the 100th playing of the Grey Cup football encounter, began with the split with his pop-star paramour Selena Gomez. Then came his accosting on stage at the American Music Awards by Jenny McCarthy, whose cougar-woman smooch-attack caused the red-blooded Biebs to react with peculiar revulsion.

Moving on, no doubt rattled, the normally well-mannered 18-year-old Ontarian was photographed receiving a Diamond Jubilee Medal from Stephen Harper in Ottawa. The Prime Minister wore a suit; Bieber wore overalls and a baseball cap discourteously backward, like a punk. (Elvis, in comparison, wore his Sunday best and bodacious when he shook hands with President Richard M. Nixon in 1970. Granted, the King's jacket was worn off the shoulder, which some saw as jaunty or even disrespectful. Others, however, interpreted it as a highly-nuanced apparel gesture.) More ignominy followed yesterday when Bieber was knocked off his YouTube pedestal by a portly South Korean curiosity named Psy. The latter's wacky Gangnam Style video eclipsed the viewership of the former's sincere Baby vignette from 2010.

And now, with his tricky intrusion into the Argo-Stampeder affair, Bieber risks the chance of being booed by boozed-up revellers at Rogers Centre. Remember that Justin Timberlake – the singer whose musical transition from boy to man Bieber now attempts to replicate – was jeered and pelted with water bottles at a 2003 concert in Toronto. That event (with the Rolling Stones, Rush and AC/DC) was in benefit of Toronto's tourism industry, which had suffered as a result of an outbreak of SARS (severe acute respiratory syndrome).

The Grey Cup crowd is not of Bieber's tween demographic. Beyond that, Bieber will be following (after performances by Call Me Maybe singer Carly Rae Jepsen and her fellow British Columbians Marianas Trench) the iconic Canadian troubadour Gordon Lightfoot. This man was singing "Gitche Gumee" two decades before baby Bieber ever heard his first "kitchy koo."

With the celebration of the Grey Cup's century-long history, the idea was to nod to the future (Bieber and Jepsen) as well as to the past (Lightfoot). The same notion applies to a pre-game show, with current hot-stuff Johnny Reid and older rocker Burton Cummings. "Anything that makes it to a hundred has to keep reinventing itself to some extent," said Sara Moore, the Canadian Football League's vice-president of marketing.

Sound wisdom, that. Bieber and his handlers hear and know it too. The pop star is just trying to make it to 20, let alone 100. This is third-down territory – no thinking of punting or single-point rouges for him now.

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