[W.]

With an award-winning actress
The religious movie star too,
The top Hollywood personality with a controversial past and his wife,
The TV star
The media personality and a glamour model,
Here on Sexahol Isle.

[JediJones]

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.”

http://www.ranker.com/list/women-who-charlie-sheen-has-dated/celebrityhookups?format=SLIDESHOW&page=4

Also, Tamara Beckwith is on the list, who Wikipedia says is a British TV guest and presenter, so she could be the “media personality.”