He wasted no time in referring to PR stereotypes, amusingly wondering if PRWeek would be handing out 'an award for the longest lunch', but his one-liners went down a storm with an audience waiting to hear if they would be later joining him on stage to pick up the trophies.
A flurry of anti-US jokes caused Diary to glance nervously across to the Ketchum tables, where the agency's three - all American - global, European and UK CEOs were seated.
But one quip 'Americans - don't be alarmed, think of this as friendly fire!' even saw global CEO Ray Kotcher turn to European CEO Jon Higgins to - we think - comment 'That's good!'.
The laddish Frank PR, meanwhile, deserve a mention for managing - while on stage collecting an award - to get Carr to plug the agency's racing greyhound Flying Frank's next outing at Walthamstow dog track. Carr looked baffled but sportingly played along.
As the wine flowed, ex-journo and Chime bigwig Kevin Murray was overheard reminiscing about an incident from his former story-chasing days in Johannesburg.
Murray, it emerged, once walked into the middle of a gunfight, and then took the sensible option: he waited until someone won, walked over and asked what was going on, before legging it back to his office shouting 'Stop the press!'.
Had the ceremony included the category 'Most booze consumed by a PR firm, per head, at one event', the winners would have been difficult to choose - but Switch Communications would have been in with a chance.
The start-up outfit's founding duo Matt Wood and Paul Doran had clearly had a well-oiled evening, with the latter jovially demanding, well into the early hours, to be taken to the penthouse, while trying to hand us promotional matches.
On a related note, former Cohn & Wolfe man Brandon Stockwell later lured Diary over with an outstretched arm and regaled his audience with the tale of one director who had spent the previous night on his floor.
The reason? Lack of electricity. The company? Switch.
Were PRWeek handing out an award for best-dressed PR man it would have been a toss up between Tulchan founder Andrew Grant and Propeller's Matin Loat, both of whom sported what appeared to be a collarless velvet suits.
Meanwhile The Number's director of comms William Ostrom was musing that the industry gongs had almost inspired him to set up his own agency 'because you get to work with all this great totty', before quickly rebuffing some cheeky leading questions from Citigate Dewe Rogerson MD Deborah Saw. We await details of the 118 118 man's next project.
Brands2Life co-founder Giles Fraser was whipped onto the dance floor before we could congratulate him on winning an award.
Others clearly enjoying their evening included Brian MacLaurin, who Diary first bumped into while he was getting changed in the Grosvenor House loos before the ceremony had begun.
In addition to indulging in his customary ready banter, MacLaurin wanted to talk about his concerns for the PR industry - albeit in his own colourful way.
He said: 'When you go to see a doctor or even a gynaecologist, you don't start quibbling with him over payment or his quality standards. But there's so much less certainty over these things within the PR industry.'
Diary hopes MacLaurin's future visits to, er, any gynaecologists continue to be hassle-free.
Go to PRWeek.com for full details of the winners, finalists and commended entries, and video footage from the event.