Cape Town – Playboy founder Hugh Hefner – who died at 91 on Thursday – lived a long and rich live. With lots of moments that will forever be etched into pop culture; from his TV cameos to most famous friends.
We’ve done some digging on YouTube and found some of the mogul’s more random moments from flying to London with a bevy of beautiful women to appearing in music videos and having Paris Hilton sing happy birthday to him.
Here are 5 random Hugh Hefner videos on YouTube:
1. Weezer’s iconic video for their song Beverley Hills (which was filmed at the Playboy mansion and features a cameo from the man himself):
2. Paris Hilton singing happy birthday to him in a very skimpy outfit:
3. When he flew into London on the world’s most expensive private jet (at the time) The Big Bunny with lots of beautiful women:
4. A rare game show appearance as a young man:
5. When Hugh got down with Justin Timberlake and Nelly in the video for Work It:
READ NEXT: Take a look inside the Playboy Mansion