had its fair share of guest stars over the years. Some became longer-term recurring characters while others were on the series for one or two episodes. Some of these characters became very memorable to audiences, such as Rose, who stalked both Charlie Harper, played by , and later on, Walden Schmidt, played by . Others, such as Enrique Iglesias and Heather Locklear, made less of an impression on viewers, despite their celebrity status.

Given that was on for 12 seasons and amassed over 260 episodes, guest stars had to be something special to stand out among the sea of characters that walked in and out of the lives of Charlie and those close to him. To do this, either the actor had to be over the top or the writing had to be spot on. Sometimes, those making an appearance on the show were lucky enough to check the box of both categories.

Other times, a guest star could do deadpan comedy and steal the scene they were in. This was the case for one celebrity that fans call "pure gold" as a guest star and made such an impression that fans wished she was on screen for longer than she was.

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