On Friday night, the hip-hop artist and businessman, and of course Beyoncé, joined Hillary Clinton on-stage at a campaign rally in Cleveland, in the key swing-state of Ohio.
"This other guy [Trump], I don't have any ill will…he cannot be my president," Jay Z said on Friday evening. "He cannot be our president. Once you divide us, you weaken us. We are stronger together." (He then introduced "the next president of the United States, Miss Hillary Clinton.")
On Friday night, Trump retaliated by incorporating Jay Z into his stump speech, a tactic he continued to use into Saturday morning.
"I didn't have to bring...Jay Z [to get a big crowd],” Trump boasted at his own rally. "I'm here all by myself. Just me, no guitar, no piano, no nothing.”
On Saturday morning, Trump kept talking about the Clinton-endorsing,Obama-loving rapper—and the rapper’s filthy, dirty lyrics.
"We don't need Jay Z to fill up arenas...we do it the old-fashioned way,” Trump said at his rally in Tampa, Florida. “I actually like Jay Z, but the language last night, ohhhh...I was thinking, maybe I'll just try—should I use that language for one of mine?”
The crowd responded to the question with loud boos.
“Can you imagine if I said that?” Trump continued, taking to bashing the more R- and PG-13-rated words in the rap lyrics. “So, he used every word in the book...last night. He used language last night that was so bad, and then Hillary said, ‘I did not like Donald Trump's lewd language.’ My lewd language?...I've never said what he said in my life! But that shows you the phoniness of politicians.”
It wasn’t just Trump using “lewd” or coarse language that got him in trouble. Last month, he was caught on tape bragging about being able to get away with sexually assaulting women due to his celebrity status. But conservative, pro-Trump rebuttals to the 2005 Access Hollywood “pussy” tape have often attempted to change the subject to simply naughty language.
In February, Trump also repeated an audience member who called GOP rival Ted Cruz a “pussy.”
At least in public, Trump has for years claimed an affection for Jay Z, however shared or unreciprocated the emotions might be. As recently as November of last year, the real-estate mogul was calling Jay Z a “good guy,” when asked by Yahoo News.
“I really like Jay Z but there is trouble in paradise,” Trump tweeted in May 2014, weighing in on the big news of the leaked security-footage of Solange attacking Jay Z in an elevator. “When his wife's sister starts whacking him, not good! No help from [Beyoncé] leads to a mess.”
But when the entertainer became politically active, Trump seemed to have no more niceties for him.
In late 2012, Trump went after President Obama for fundraising and campaigning with the rapper in times of crisis:
In the past, Trump has been something of an aspirational figure referenced in many rap songs, prior to his divisive presidential run and racist birther crusade. And in the New York high-society scene, he and Jay Z would sometimes rub shoulders at public events.
For instance, at a fashion show in 2002, Trump actually sat with Jay Z and none other than Monica Lewinsky at an event for designer Luca Orlandi.
Trump was later listed as a sponsor for a presidential fundraiser for Al Sharpton, who sought the Democratic nomination in 2004. Also on the list of sponsors was Jay Z and Russell Simmons (who is now also a Clinton supporter).
At the time, Trump claimed he had no idea why his name was on the roster, telling the New York Post: "It's a ridiculous situation. I know nothing about his campaign, I know nothing about his party. Nobody ever called me about it. I like Al Sharpton, but I'm not supporting him."
In the past year, evidence surfaced that on Jay-Z’s part there’s no love lost. Last Week Tonight host John Oliver claimed in March that Jay Z contacted the network to get one of his “Make Donald Drumpf Again” hats, which was meant as a dig on Trump’s family’s original last name when they came to the United States.