In Kanye West, Donald Trump has found his platonic ideal of a supporter: someone as, if not more, famous than he, who touts the virtues of dragon energy and manhood, and pushes back against the idea that the current presidency is built upon racist tropes and policies.

In Donald Trump, rapper Kanye West has found something perhaps even more satisfying: a president who can actually stand him.

The relationship has been curious and confusing and the perfect catnip for cable, especially on Thursday, when West attended his latest meeting with Trump, this time in the Oval Office and for lunch at the White House with senior staffers and former NFL running back Jim Brown.

Much of the Oval meeting, which was open for press and news cameras, quickly degenerated into the Trump-loving music icon going on a prolonged, shape-shifting, often surreal, and nonsensical soliloquy as the president looked on from across the Resolute Desk, transfixed and seemingly impressed.

“Let’s stop worrying about the future, all we have is today,” West said. “Trump is on his hero’s journey right now. He might not have thought he’d have a crazy motherfucker like [Ye].”

There was more. A lot more.

West touched on the controversial policing practice stop-and-frisk. He claimed he was misdiagnosed with bipolar disorder, and was instead simply sleep-deprived. He mentioned the concept of “Yeezy ideation centers." He even pitched having Apple make Trump an “iPlane” to replace Air Force One. “We’ll get rid of Air Force One,” Trump replied.

West also said Trump had inspired him to sign a contract with shoe and clothing design company Adidas. “You gave me the heart to go to Adidas,” he told the president. “This Adidas thing made me a billionaire.”

It was a love fest, one that culminated in a big hug, with West announcing, “I love this guy.” For those in the political arena who have dealt with the megastar rapper before, however, it felt a bit like deja vu. Thursday’s meeting wasn’t even the first time Kanye West had rambled to a sitting American president about Adidas.

The last time the rapper did that, the then-president, Barack Obama, seemed much less amused. The two of them had a slightly more complicated history.

“Kanye was a big supporter ours in 2008, we flew around the country doing get-out-the-vote concerts together—and that all fell apart after Obama was caught on a hot mic calling Kanye a ‘jackass’ [in 2009, in response to the Taylor Swift incident],” Dan Pfeiffer, a former senior adviser to President Obama, said in an interview on Thursday afternoon, shortly after the new West-Trump footage aired.

Pfeiffer, who also recounted a version of this story in his book Yes We (Still) Can, said that West and Obama had zero contact until shortly before the 2014 midterm elections, when West and Kim Kardashian paid to attend a Democratic National Committee fundraiser consisting of roughly 25 people. Obama was speaking at the event and taking questions in the study of the host’s home—and West ended up seated on a couch right in front of Obama.

“We were nervous about [Kanye] coming, because we didn’t want a blow-up that would dominate the news in the run-up to the midterms,” Pfeiffer recalled. He said that West sat quietly during the event, right until Obama said he would take one last question.

West raised his hand, and subsequently delivered a lengthy monologue that was “not unlike today’s,” Pfeiffer noted. West even invoked Adidas, though it was in the context of ruminating on famous feuds and enemies.

“The takeaway was, Kanye and Obama had a lot of similarities,” Pfeiffer said. “They were both from Chicago, both raised by a single mom, everyone loves them.” West then went on about how “everyone has opponents”—Nike and Adidas, Coke and Pepsi, Kanye and Drake, Obama and Republicans.

According to Pfeiffer, no policy was mentioned during West’s homily, which lasted for approximately 20 minutes—roughly twice as long as the riff with Trump in the Oval on Thursday. “There was no time anyone could cut him off,” Pfeiffer explained, because he “barely paused” as he spoke at Obama. Finally, the 44th president jumped in, thanked West and quickly departed with his entourage.

As their limo departed, where Obama sat with Pfeiffer and fellow aides Valerie Jarrett and Anita Decker Breckenridge, the president briefly reflected on his interaction with West. “That shit cray,” Pfeiffer recalled Obama saying, in reference to the Jay Z and Kanye West song “Niggas in Paris.”

Pfeiffer says he never heard Obama ever bring up West’s name after that evening.

There was, of course, a time years ago when Trump’s attitude toward West more closely tracked with Obama’s.

In 2009, the day after West’s infamous stunt against Taylor Swift at the VMAs, TMZ caught up with the then reality-TV star and future president for his thoughts. Trump told TMZ that West’s conduct was “disgusting,” and actually advocated boycotting West “so this kind of thing doesn’t happen” anymore. “He couldn’t care less about Beyoncé,” Trump continued. “It was grandstanding to get attention.”

The following year, the award-winning rapper released a 2010 song titled, “So Appalled,” which includes the line, “Donald Trump takin’ dollars from y’all.”

The pair have come a long way in the span of eight years. Indeed, a source close to Trump told The Daily Beast this week that the president “lights up” nowadays when privately talking about West’s support and the A-list friendship and what it is supposedly doing for him and the black vote.