The “top Hollywood personality with a controversial past” could be Heidi Fleiss. Sheen used her brothel. Nothing seems to say he slept with her though.
The TV star could be Denise Richards. I think she was more of a movie star in the ‘90s, but looks like she’s been in more TV shows and TV movies lately.
This list of Sheen girlfriends includes one described as a “glamour model.”
Also, Tamara Beckwith is on the list, who Wikipedia says is a British TV guest and presenter, so she could be the “media personality.”
Bruce Jenner?