Dean Winters: Dean Winters. Actor: John Wick. Dean Winters is known for his role as Ryan O'Reily on HBO's award-winning series Oz (1997) and as Tina Fey's character's "Beeper King" boyfriend on the Emmy-winning comedy, 30 Rock (2006). His noteworthy comedic performance was recently included in Entertainment Weekly's "Must List" as well as Variety's short-list of Emmy-worthy guest performances. In addition to being featured in the film P.S. I Love You (2007)...