Holly Madison
Self

Hugh Hefner
Self (archive footage)

Stacy Arthur
Self

Joseph DiMartino
Self

Kendra Wilkinson
Self (archive footage)

Bridget Marquardt
Self - Former Playboy Model / Self (archive footage)

Jeana Keough
Self

Emily Pokora
Jasmine Fiore

Sarah Moliski
Star Stowe

Bobby Liga
Jon Logan

Talon Reid
Self - Kelsey's friend

Tia Barr
Mandy Bentley

Conan O'Brien
Self (archive footage)

Brande Roderick
Self (archive footage)

Jon Stewart
Self (archive footage)

Ben Stiller
Self (archive footage)

Christine Taylor
Self (archive footage)

Mia Farrow
Self - Rosemary (archive footage)

Sharon Tate
Self (archive footage)

Victoria Vetri
Self (archive footage)