* CrackPairing: Would you believe that there is actually a very large portion of fanfiction writers that 'ship Will/Karen?
* CrazyAwesome: Karen, full stop.
* EnsembleDarkhorse: For most people, either CrazyAwesome Karen or Snarker supreme Rosario.
* FairForItsDay: Offensive as it may have sometimes seemed by the time it ended, it was one of the first American shows with a gay man as a central character, and remains one of few not relegated to cable at midnight.
** Additionally, the show's original run happened right during the tipping point of cultural acceptance of homosexuality. As such, it started out as a landmark step forward to have two gay leads on a popular network show in prime time. However, as homosexuality became more socially acceptable and more serious material was made, the show seemed less fresh and daring.
** One interview with the creators indicates that they were fully aware that they were at a tipping point in social attitudes and were trying to play a delicate balancing act. Essentially they knew that they couldn't have a StraightGay character like Will without part of the audience saying "That's not what ''real'' gay people are like!" and they couldn't have a CampGay character like Jack without the other part of the audience saying the same thing. So they put both in there and hoped they balanced out. The fact that Will became a bit more camp over time was most likely due to RuleOfFunny, but also possibly the fact that Jack started getting episodes that took his feelings and emotions seriously too... they were still in balance.
* FamilyUnfriendlyAesop: Often, but never to be taken seriously.
* FreudWasRight: Jack has the classic Freudian family pattern for homosexuality, but the trope's averted with Will: he's always had a good relationship with his father, and was close to his older brother Sam until he told Sam what he thought of Sam's fiancée. Will is, however, his mother's favourite. Will's gay friend Larry also appears to be very close to his mother. Elliot, on the other hand, also has the classic family pattern for homosexuality but he's straight as an arrow.
* HollywoodPudgy: Jack regularly calls Will fat, but is the only one to do so.
** There were a few rare barbs thrown at Grace by Karen (who usually called her boyish and flat-chested instead.) However, this showed clearly that this was deliberate. A few critics mentioned that the fat jokes thrown at Grace weren't as funny when Debra Messing was pregnant, showing that this was supposed to play off the ValuesDissonance of making fat jokes toward the slender [=McCormick=] and Messing, similar to the fat jokes made toward Vivian Vance during ''ILoveLucy.''
* LesYay: Karen and Grace got to kiss far more than Will or Jack ever did.
** Karen also has quite a bit of FoeYay with Lorraine. Best summed up when Lorraine was trying to steal some of Karen's jewels. After the takes off the visible jewels, and the ones hiding in her cleavage, Karen merely responds, "And...?" Lorraine then spreads her legs further apart and ''more jewels fall to the floor.'' Karen's response? "Impressive. Had we met under different circumstances, this might be 'hello' instead of 'goodbye.'"
*** Also in one episode, Karen mentioned having a crush on someone with long blonde hair as a kid, but she couldn't remember whether said crush was male or female.
* RetroactiveRecognition: In "Fagmalion" part four, Karen dated a handsome, intense maintenance man named Anton. About seven years later, his actor is providing the voice of a [[PrincessAndTheFrog handsome, less-than-intense prince-turned-frog.]]
** She also once had a Thanksgiving hookup with a plumber, at Stan's behest--played by Mullally's real-life husband Nick Offerman, now well-known as [[ParksAndRecreation Ron Swanson.]]
* ValuesDissonance: Partway through, they started to imply VagueAge with Karen, joking either she made a deal with the devil, or was so perpetually filled with pills and alcohol, she was somehow pickled and therefore immortal. She then would occasionally make a comment that would sound more appropriate coming from a bigoted person from the turn of the ''last'' century. She refused to believe that a woman could be a doctor, and when Rosario once said that she played Maria in a production of ''The Sound of Music,'' Karen said she would have paid six chickens to see that (Rosario's response: "It was an Equity Theater, you racist bitch.") Frequently she comments that she believes than El Salvador (where Rosario is from) is come dusty, barren SouthOfTheBorder LatinLand stereotype.