Towards the end of the show, Tony Soprano is watching "The Sopranos" home movie. This home movie is circa the 1960's. The vehicle that is shown in this home movie has the current yellow New Jersey license plate design which came into existence in the 1990's.
Tony is arrested at his front door. As the cop cuffs him, the camera gives a closeup of the handcuffs being hooked up. Tony's right is cuffed, then as the actor playing the cop goes to cuff Tony's left, he pushes the wrong side of the cuff against Tony's wrist. The camera cuts away and you hear the cuff ratchet closed but there is no way the cuff would have gone on.