Donald Trump Roast Revisited: What Comedians Weren't Allowed to Say and What Jokes Cut the Deepest

When Donald Trump was the focus of a Comedy Central roast in March 2011, everything, including his children and wife, was fair game except for one topic - his wealth.

The billionaire businessman was riding high at the time thanks to his hit reality show, The Apprentice. On a stage decked out in gold, naturally, Trump was taken apart by one foul-mouthed comedian after another, framing attacks about everything from his hair to his perverted thoughts about his own daughter. Seth MacFarlane served as roast master.

"By the way, Donald, it's pronounced 'huge,' not 'uge.' Also, it's pronounced 'I am f - ing delusional,' not 'I am running for president.'" MacFarlane quipped.

Trump made headlines before the roast when he announced he was considering throwing his hat into the ring to be president for the 2012 race. Some of the comedians involved in the roast encouraged him to run. Trump, who gave somewhat of a tiny stump speech when it was his turn to fire back, said he participated in the Comedy Central event for charity. Yet, at least one of the comedians involved says he always believed Trump had ulterior motives.

The Hollywood Reporter recently caught up with comics Anthony Jeselnik and Lisa Lampanelli, who each took hilarious and sometimes even cringe-worthy shots at Trump during the 2011 roast. They explained what they weren't allowed to say and which jokes seemed to hurt the now presumptive GOP presidential nominee the most.

"Trump's one rule was 'don't say I have less money then I say I do,'" Jeselnik tells THR. "His kids were fair game. His wife was fair game. And I remember one of my jokes was about his casino business failing, and I could feel that hurt coming off of him. He didn't like that joke, and I told a joke about people being glad he has cancer," he says in amazement.

The cancer joke: "Donald, I'm not sure if you're even aware of this, but the only difference between you and Michael Douglas from the movie, Wall Street, is that no one's going to be sad when you get cancer."

Jeselnik still chuckles when he remembers the moment. "I called him a douchebag to his face and that wasn't as harsh as saying 'you don't know how to run a casino.'"

While reminiscing about that night, one he calls a favorite of his career, Jeselnik explains he was at first confused as to why someone like the billionaire businessman would volunteer to be ripped apart. Then it clicked.

"I remember thinking at the time that 'he's going to run for president,'" Jeselnik tells THR. "There was no reason for a guy like Trump to put himself through that. And I remember thinking 'he thinks we're going to punch ourselves out.' Like, we're going to say every mean thing that can be said, and then he kind of has a free pass to the White House."

Trump's Comedy Central roast was Jeselnik's first. He went on to be a part of two others, for Charlie Sheen and Roseanne Barr.

Lampanelli knew Trump could take a joke because she participated in a Friars' Club Roast of Trump years before the Comedy Central event, so the "Queen of Mean" was more than ready to tee off on the real estate mogul a second time around, she says gleefully.

"I noticed during that [Friars'] roast that I kept elevating jokes as I went along to determine what he could take, and he just loved every one of them," Lampanelli says. "So when they decided to roast him on Comedy Central a few years later, it was so easy because I was like 'this guy can take anything.'"

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Trump didn't fake being a good sport, he actually was one, Lampanelli remembers, but she also recalls jokes about his bankruptcies being off-limits for the Comedy Central event.

"I didn't have any [bankruptcy jokes] anyway so I didn't have to cut anything," she says. "So when I sent in my roast jokes, they were like 'yeah, these are all approved, these are all great.' And they were all really edgy jokes, in fact one may have been my edgiest joke ever."

That joke: "You've put up more worthless hotels than an autistic kid playing Monopoly."

Lampanelli has also participated in numerous roasts, including those for Pamela Anderson, William Shatner and David Hasselhoff.

While the two comedians agree that Trump's Comedy Central roast was one of the best, they have differing opinions on just how much Trump enjoyed himself.

"I was surprised because I thought it was all an act ... but he was genuinely really into it and he even went up to us individually at the end of the night and said 'thank you so much, that was so hilarious' and quoted jokes and stuff," Lampanelli remembers.

Jeselnik contends it appeared to him that Trump was "playing the role" of someone having fun and insists, in his opinion, there was more to the evening for Trump.

"At no point did I think he was actually enjoying himself," Jeselnik says. "I totally believed he had a game plan. He volunteered for it and it seemed smart in a way. Like, 'let's get the pros out here and really tear me a new one and then in five years when I start to run [for president], these things will kind of punch themselves out.'"

Jeselnik backs up his theory by saying that Trump had to be told more than once he needed to actually smile during the evening. At one point, Jeselnik says, a fellow comedian and roaster had a word with Trump about his lack of reaction.

"Jeff Ross told him 'the more you laugh, the more this is about you, the more the camera is going to find you when you're laughing,'" Jeselink says. That tip did the trick, he adds.

Lampanelli, who also worked for Trump when she appeared on Celebrity Apprentice, jokes it's possible Trump was just smiling because "he just loves to hear his name mentioned no matter what the context is."

Calling Trump the "best roast topic ever," Jeselnik says the would-be politician worked best for that type of comedy format because he evokes such little sympathy from others.

Still, Jeselnik says he would have altered portions of his material had he been keyed in on something he's aware of now.

"I wish I had known about the small hands thing," he says. "If I would have known he was sensitive about his hands, that would have been five jokes."