Donald Trump turned cheering of the guests to booing at a fundraising dinner on Thursday night, as he directly attacked Hillary Clinton in a scathing speech.
The dinner, a staple fixture towards the end of recent presidential campaigns, is normally embraced by candidates as an opportunity to showcase self-deprecating humour and land lighthearted jabs on their opponent.
Diners on Thursday however booed for the first time in years as Trump missed the mark with his bruising put-downs.
The Republican candidate was first to speak at the Alfred E. Smith Memorial Foundation dinner at the Waldorf Astoria Hotel in New York, taking to the microphone after an icy encounter with his opponent before dinner.
He started well, sending the room into roaring laughter with an unexpectedly self-deprecating sense of humor.
They turned on him when his jokes evolved to insults, accusing Clinton of 'hating Catholics' and 'corruption'.