10. Gary (Michael Rapaport) – THEN

Talking of men in uniforms… Phoebe definitely has a thing for them, doesn’t she? Gary was that one policeman who bumped into her after she’d found his badge and was using it to take the law into her own hands. When Gary turned up at the apartment later asking for Phoebe, she immediately assumed that she was about to be arrested. However, Gary surprised her and the gang by instead asking her out to dinner.

The two dated for a little while, but everything went sideways when Gary asked Phoebe to move in with him. After waking up on a beautiful morning, Gary shot a bird singing outside the window. Phoebe immediately ended the relationship.

Since appearing on Friends, Michael Rapaport has directed for himself, and continued acting. One of his most notable appearances was his recurring role in My Name Is Earl, and for starring in blockbusters such as Deep Blue Sea. He’s also tried his hand at stand-up comedy, and has even dabbled in the art of voice acting.

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Michael Rapaport (Gary) – NOW

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