Diddy Tries to Teach Romance, Explains Why Times Square Billboard Is So Meaningful on Carpool Karaoke

The iconic hip-hop mogul took the late-night host through some of his biggest hits, but the best bits of this segment came between the songs. It started right at the top with James trying to get a bead on what to call his passenger.

"You can call me any of the approved names," Diddy told him. "I was born Puffy and then I became P.Diddy. Then they called me Diddy because I was so pretty. And then Puff Daddy and then I became who I am now, which is Love. L-O-V-E, not Brother Love, just Love."

James took a beat and then pointed out that there was one name that seemed to be missing from that list. "I can't help but notice that you've overlooked Sean," he told the artist born Sean Combs.

Diddy explained that this name is held in reserve for only two people. He also joked that when he hears it, it sounds like "when you're in trouble or something like that ... so that's not on the approved list."

Other than his mother, he said there is only one other person allowed to call him Sean, and that's because he also calls this individual Shawn. That's because Jay-Z's real name is Shawn Carter.

As each name reflected a different era in Diddy's life, James asked him what name he should consider for his own next chapter, with his tenure on "The Late Late Show" ending next week.

When Diddy asked him what he wanted this next chapter to be, he said, "joyous, uplifting, fun." With this, Diddy decided they should share the name Love as that's what he's about right now, too.

Next up the pair took on Diddy's self-titled track, "Diddy." But it was too much for James, who afterward could not get over the fact that in the chorus of the song, they spell out "D-I-D-D-Y-D-I-D" and then move on to say the name.

"It's Diddydid," he kept insisting, while Diddy tried to explain to him that it's not. Finally, he tried telling James, "The last D and Y are silent," but that didn't sway him, either.

But most uproarious segment came later when James brought up Diddy becoming a father for the seventh time. When he asked, "How does that happen?" Diddy took him literally and said it was all about the music.

The two then went into a very long, very wild and very funny journey through how to properly set the mood and woo your women through the entire length of an album. "The album is purposely long for the stroke," Diddy explained after James quipped it would take 28 seconds, "not the pitter-patter."

Things took a serious turn for a moment when James asked about the massive billboard Diddy bought in Times Square and held for years and years. When James asked him why he wanted to do that and hold it for so long, Diddy explained that it's because he's a "disruptor."

"I'm a disruptor, so just coming to disrupt the world in the sense there was never a Black person that I saw in Times Square on all these billboards and that affected my psyche," he explained.

"So when I got the chance, I said I want the biggest billboard in Times Square and I want my my fist to be raised to the end so all the children around the world, when they come to Times Square, they can see that anything's possible."

The clip then ended with a very touching moment of inclusion for James, who was invited to be the third person approved to use the name Sean.

All in all, this was one of the most enjoyable and delightful "Carpool Karaoke" segments we've seen. We found ourselves laughing and smiling almost as much as Diddy and James all the way through!