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I think the better move (if you're determined to bluff at it) is to lead out with a bet. It's a high card flop with only one low. So go ahead and put pressure on the low draws.

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The problem with leading is that Barry's hand has just about no value. Nor does he know yet that the pre-flop raiser nor anyone else doesn't like their hand enough to bet. Leading out for a bet will offer his opponents something like 10:1 to continue. Barry's hand is pretty miserable and betting out has little/no fold equity. I don't like that play at all. I assume Barry would have check-folded if the flop action had transpired in any other way, and he decided to get a little tricky and check-raise only because everyone else checked to the button who bet.

Edit: I'm only saying Barry's play is not terrible because I'm assuming the players in the big game are solid enough to fold a lot of hands for two bets cold. The crux of the play is the fold equity his raise generates from the players in the middle and also the button. If this was a PartyPoker $0.50-$1 table, then check-raising is suicide. In the big game, I'm guessing it's reasonable.

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It's worth noting that even if this play is slightly -EV right now, it will probably pay dividends on future hands where he actually has a hand and the same action occurs.

I'm not sure that's the case, but it's something to consider.