 He has a "gang" of friends who embark with him on his everyday trials and tribulations.Drew's friends include erudite but unambitious Lewis (Ryan Stiles), excitable dimwitted Oswald (Diedrich Bader) and his friend (later on-off girlfriend) Kate (Christa Miller).In the final two seasons, Kate gets married and moves to Guam, in the same two-part episode that introduces and develops Drew's relationship with Kellie (Cynthia Watros), which carries on over the final two seasons.