The 16 Best Friends Guest Stars, Ranked – Looper

In 1996, well before Charlie Sheen was on the biggest sitcom on TV with “Two and a Half Men” (and then got fired for “winning”), Sheen guest starred on “Friends.” It was Season 2, Episode 23, “The One with the Chicken Pox,” and Sheen’s Ryan comes to see Phoebe and, as the title suggests, gets chicken pox. See, Ryan is a sailor in the United States Navy who spends most of his time on a submarine, only resurfacing every couple of years, at which point he goes to see Phoebe. This time, though, Phoebe, the only friend who hasn’t had them as a child, gets chicken pox because of Ross’s son. Unfortunately, Ryan hasn’t had them either and, when he makes a grand gesture of kissing Phoebe despite the pox, he gets them himself.

This leads to a two-week furlough spent getting over chicken pox with Phoebe. Instead of a romantic time going to places around New York, the couple spends their time in Monica’s apartment trying — and failing — not to scratch. They even have their hands taped up with oven mitts to avoid scratching. It’s not a noteworthy shore leave for Ryan, but for Sheen, it was a tour de force of comedic talent and timing that ultimately landed him this high on our list of “Friends” guest stars.