Spin City
Workaholic Mike Flaherty is the Deputy Mayor of New York City, serving as Mayor Randall Winston's key strategist and much-needed handler. Mike runs the city with the help of his oddball staff: an anxious and insecure press secretary; a sexist, boorish chief of staff; an impeccably groomed gay activist running minority affairs; a sharp and efficient, man-crazy accountant; and an idealistic young speechwriter. Like Mike, they are all professionally capable but personally challenged.

Season 5 · Episode 2 ·
Smile
Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractive. Carter and Stuart deal with someone who keeps parking a bike in their parking space.
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Episode 2 of season 5 of Spin City: “Smile”. Aired 2000-10-25. Watch it online free on ZapFlix.