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Comedians Give Marco Rubio Advice On How To Roast Donald Trump

The Huffington Post logo The Huffington Post 29/02/2016 Sam Stein

The future of the Republican Party rests on the potency of a dick joke.

Barnstorming his way through Super Tuesday states these past few days, Sen. Marco Rubio (Fla.) has mocked Donald Trump as a pants-pissing spoiled rich kid who can't spell and has tiny, tiny hands.

It hasn’t been the most elevated stuff.

Now, Rubio’s supporters argue that since Trump has gotten wall-to-wall coverage by being a childish, outlandish bully, Rubio himself should be able to give it a try. And if the media objects, well, screw them and their sudden high-mindedness.

Fair enough. But there’s a bigger question for the senator than whether this new tactic is “presidential.” And that is: Does it actually work? Can you beat Trump at his game? And if humor is indeed the antidote, is Rubio doing it right or particularly well?

To answer these questions, The Huffington Post asked people who have roasted Trump before, as well as comedians and comedy writers. None actually begrudged Rubio for going down this path.

"What are you going to do, make fun of [Trump's] policies? He doesn’t have any policies!" said Neal Brennan, who co-created "Chappelle's Show" and currently is doing a stand-up show called "3 Mics." "There is nothing else to go for."

But others questioned whether the Florida Republican had the right touch to actually chip away at Trump's support or even bait him into reacting badly. Comedian Rob Delaney, co-writer and -star of the comedy series "Catastrophe," for example, said Rubio is simply incapable of humor.

"He will never be funny. He has no conviction, no authority, no confidence. Mitt Romney is funnier," said Delaney, who also listed Trump, President Barack Obama, New Jersey Gov. Chris Christie and former President George W. Bush as occasionally funny political people. But not Rubio.

"You have to care about something to be funny," Delaney said. "What does he care about? Advancing his career? He has no other defining qualities or characteristics."

There is precedent for using humor to make Trump squirm. In 2011, during his speech at the White House Correspondents Dinner Obama mercilessly mocked the businessman -- producing the lasting image of a brewing Trump sitting emotionless as the entire room laughed at his reality television career.

That same night, Seth Meyers piled on, wondering what dead animal was living atop Trump's head. And then there was the Comedy Central roast of Trump that same spring that was, well, a series of jokes about Trump being so egomaniacal that he masturbated to himself.

It's unlikely that Rubio will go there (though the fact that we had to use the word "unlikely" is really something). But what about the other material?

The writers of it aren't sure if it can work again.

“I don’t want to express a strong opinion because we are in this totally insane moment where the conservative elite of Washington have been begging Marco Rubio to call Donald Trump's penis small and they’re like, 'Finally!'" said Jon Lovett, Obama's former speechwriter who along with several others and Judd Apatow, worked on the 2011 Trump bit. "Everything is super weird now.”

Brennan, who worked with Meyers on his 2011 speech, worried that even the best Trump jokes would only make his fans love him more. "If you hire ten great comedy writers you will have better jokes," he said. "I think this is the lowest hanging fruit that Rubio can find. And I don’t think it is going to help because I think Rubio is too little and sweaty to win. He is the Latino Bobby Jindal. But I think it is his best shot."

So what could work? Delaney isn't sure that anything will, so long as Rubio is the one delivering the lines. The small hands joke, he said, seemed "scripted to death."

"Another big ingredient in humor is spontaneity, or at least seeming spontaneity, which is what separates the professionally funny from civilians," Delaney said.

But Travon Free, who writes for "The Daily Show," said there is a joke -- perhaps too risqué though -- that would work. And one that clearly drove Trump insane when they used it: mocking his weird infatuation with his daughter Ivanka. 

"Nothing else sticks. No matter what you say, he has a comeback for it or he dismisses it or he hits you hard," he said. "This is how you destroy Trump. Talk about the fact that he wants to bang his daughter. That is a weird thing for someone who wants to be president."

Free didn't expect Rubio to follow his advice, even in an election where the establishment pick is the one telling the dick jokes. Going after the daughter, he explained, "is something only a comedian can do."

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