He's noticed the president doesn't like to laugh

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January 26, 2017 at 10:04 AM EST

Jeff Ross has roasted plenty of celebrities in his day, but only one of them has since become President of the United States. During his Wednesday night appearance onĀ Conan, host Conan O’Brien asked Ross to share any insights he learned working with Trump in 2011.

“It is odd,” Ross said. “He loves being roasted. I’ve roasted him twice actually, but he doesn’t laugh. So, you have to just keep going until you get him to break.”

“It’s almost like he loves being the center of attention, the attention of being roasted, but he doesn’t want to laugh at himself,” O’Brien said.

“He finds that the challenge of letting everyone know that he doesn’t think it’s funny even though he wants to be roasted,” Ross said before sharing a few of his jabs, which included several about Trump’s bankruptcy filings.

Watch the clip above.

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