She first started out with audiences viewing her as just the daughter of Lionel Richie but she quickly became the breakout star of the show.
Some of the most interesting celebrity women to pose for Playboy have come from reality television, which can sometimes make a big statement about them.
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She has worked with Playboy multiple times over the years.
Did she ever pose in Playboy? This led to the reality series, The Hills, where she was the new main focus of the show.
Did Lohan ever pose for Playboy? This was the first season of the series and she solidified herself due to her ruthless behavior in the boardroom.