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  • Ensemble Dark Horse: Stacy was a very popular character despite only appearing in 2 of the 6 seasons.
  • Epileptic Trees:
    • James had already gotten fired last season and was on Mike's payroll as the "Deputy Deputy Mayor", so when Mike left..?
    • James was re-hired as the Mayor's speech writer prior to Mike's departure, presumably due to budget cuts which meant they were understaffed.
    • The closest they got to acknowledging the disappearances of James, Nikki, Janelle, and Stacy was in Season 5's "Smile", where the Mayor (while grieving over the death of his favorite dentist) expresses lament over the fact that some people who were important to him have left within the past few months. Granted, he doesn't mention any names, but let's just say he's talking about Stacy, Nikki, Janelle, James, and of course Mike.
  • Harsher in Hindsight:
    • "Age Against the Machine" features Charlie ultimately deciding that he's too old to party every night. If only Charlie Sheen had come to that same conclusion...
    • Carla Gugino's final episode has Mike being worried that his and Ashley's differing political views and competitiveness could result in the destruction of their relationship. Ashley assures him everything's fine, and their relationship can withstand anything. Seems heartwarming, at first, but the very next episode, had Mike just been dumped by Ashley, and going through a Heroic BSoD. Damn....
  • Hilarious in Hindsight:
    • In one episode Mike and his crew accidentally hires an interpreter for Deaf people, who fakes his sign language, angering the Deaf community. This later happened in Real Life at Nelson Mandela's funeral in 2013
    • From "The Spanish Prisoner." Caitlin tells Charlie, "You're so self-confident, so self-assured, with so little reason to be that way." Considering the kind of smug Cloudcuckoolander Sheen would later become ("Tiger Blood", "Winning")...
    • On "How to Bury a Millionaire", Paul wins the top prize on Who Wants to Be a Millionaire?. Three days after the episode's original air date, John Carpenter became the first top prize winner on the real show.
    • In "Catcher In the Bronx," Mayor Winston catches a foul ball that was meant for the Yankees fielder, which would've fulfilled Roger Clemens' no-hitter. Clemens surrendered a hit to the next batter. Many were disappointed in the mayor, to say the least. Later on in 2003 in Chicago, Steve Bartman would suffer a real-life fate & a much greater burden than a mere no-hitter by catching a foul ball that, had a Cub caught it, would've surely gotten the Cubs to the World Series since last appearing in 1945. Chicago's opponent, the Florida (now Miami) Marlins, won the National League pennant instead & then the year's World Series by beating the Yankees. (Clemens was among them before becoming a Houston Astro the next season.) Marlins fans can find it hilarious. Cubs fans considered it harsh from 2003 to 2016. Incidentally Bartman was absolved after the Cubs won the 2016 World Series.
  • Ho Yay Shipping:
    • Stuart & Carter eventually started acting more and more like this. Unusual mainly because Carter was gay. Became very, very close to canon at times. (Carter's nightmarish Imagine Spot about ending up with Stuart, miserable together until death, is probably a crowning example.)
    • More and more? It already started in the second episode, with Stuart asking Carter on a date.
    • Carter eventually starts questioning whether or not his feelings for Stuart are romantic. Asked to testify that he isn't in love with Stuart, he stammers that he "doesn't know" ... and also doesn't actually deny that they've been sleeping together.
  • Retroactive Recognition: Malcolm Reynolds was a gay personal trainer in New York.
    • Denny Colt appeared in one episode as a nudist campaigning for naturist's rights.
    • Jorge Garcia (Hurley from Lost) appears briefly as a taxi driver in one of Michael J. Fox's The Bus Came Back episodes.
    • Fans of Once Upon a Time will recognize Lana Parrilla as Charlie's secretary Angie in Season 5.
    • John Francis Daley appears in a Season 6 episode playing an intellectual student who becomes fascinated with Charlie's lifestyle.
    • Andy Daly makes one of his earliest TV appearances in "The High and the Mighty."
    • Seth Meyers makes his first TV appearance in "Charades".
  • Tearjerker:
    • The fourth season finale certainly qualifies. This is emphasized by the fact that the show's usually upbeat music is replaced with sad motifs and themes, and there is a reprisal of 'Everybody Gets What They Deserve' by The Churchills, which was used in a heartwarming moment in Season 3.
    • It's even more of a tearjerker if you consider that Michael J. Fox only left because of Parkinson's. Otherwise the show might have continued.

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