Sean 'Diddy' Combs, 54, who is in jail in New York awaiting trial on charges including sex trafficking and racketeering, is said to have carried out the timings to ensure his alleged orgies were as full as possible of A-listers.
Documents and videos reportedly seen by the New York Post are said to show Combs held at least three raucous sex parties after major events in the showbiz calendar.
The Post said it had viewed footage from star-studded after parties hosted by Diddy following the 2004 and 2005 MTV VMAs in Miami - and one following the 2005 Super Bowl in Jacksonville among others.
It said one clip taken after Combs hosted the 2005 VMAs reportedly shows the afterparty descend into a wild bash, with two men allegedly captured on camera having sex with a young girl who had powder under her nose.
In another clip a couple is reportedly seen having sex on a table as others look on.
Footage from after Combs' post-Super Bowl party in 2005 are said to show similar debauched scenes at a $2 million Sawgrass mansion which the rapper is thought to have hired for $20,000 a week.
The tape reportedly shows two men having sex in front of a group of people, and the Post states another clip appears to show Combs filming from his perspective while having sex with a woman.
There is no suggestion the celebrities at the party were aware of what it apparently descended into as they had left before the videos were taken.
Prosecutors have alleged Combs' 'Freak Offs', which were sometimes-days long, involved women who had been blackmailed or coerced into taking part.
Combs maintains his innocence, and will face a jury in the spring.