Ellen DeGeneres Once Joked That She Planned to Arrive to Diddy’s Parties at 2 AM: ‘That’s When You’re Really Cool’

Hip-hop mogul Sean “Diddy” Combs has made several memorable appearances on The Ellen DeGeneres Show. In a 2018 episode, DeGeneres surprised Combs by introducing a performer dressed as Pennywise from It, leading to a hilarious and unexpected reaction from the music mogul. Earlier, in 2015, Combs participated in a lighthearted game of “five-second rule,” where he humorously requested extra time to answer questions, citing advice from his therapist to pause before responding. While these appearances endeared him to audiences, he’s now under the microscope with his federal trial. We’re looking back at the time Ellen DeGeneres commented on arriving at Combs’ parties well after they began.

Ellen DeGeneres joked about arriving at Sean ‘Diddy’ Combs’ parties at 2 a.m. in 2015

Sean “Diddy” Combs is currently facing serious federal charges, including sex trafficking and racketeering, stemming from orchestrated events known as “freak offs.” These gatherings, described by prosecutors as “elaborate and produced sex performances,” allegedly involved coercion, drug use, and sometimes violence. Victims were reportedly transported across state lines and subjected to degrading acts, often under the influence of substances. Combs’ associates allegedly helped book hotel rooms, supply drugs and lubricants, and arrange for IV fluids to help victims recover.

Before Combs’ trial began in May 2025, speculation flooded the media. Many wondered what celebrities knew about what occurred after Combs’ parties. A source previously said that celebrities knew to leave Combs’ parties before 2 or 3 a.m. “Girls would start to lose their clothes — that was the signal for people to leave,” the source told Us Weekly. However, they added, “What happened before 2 a.m. pales in comparison to what happened at 5 a.m.”

In 2015, Combs visited The Ellen DeGeneres Show. Ellen DeGeneres brought up the topic of Combs’ notorious parties.

“I was reminded that I participated in an invite for your 29th birthday party,” DeGeneres said. “Do you remember this? I don’t remember it. … I don’t think I was invited to the party. They just asked me to do something. There was, like, Oprah, and Chris Rock, and a bunch of people. …”

DeGeneres then cut to her 1998 video, which also contained Oprah and Chris Rock. She started the video by making fun of Combs’ many nicknames. “I thought his name was Puff Daddy,” she says. “Sean P., Puff, Puffy Poo. … So, at 10 o’clock it starts, so if you’re cool, get there, like the next day, at like, 2. That’s what I’m gonna do. That’s when you’re really cool. Show up the next day!”

It’s unclear if DeGeneres meant 2 a.m. or 2 p.m. However, given Combs’ reputation at the time, it’s clear that no one arrived at one of his parties in the afternoon.

How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area. 

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