These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Harsher in Hindsight: This Fire Marshall Bill skit had a part where it's implied that Fire Marshal Bill and an Arab man bombed the World Trade Center, just to prove that it wasn't structurally sound. Yes, it was referring to when the World Trade Center was first bombed in 1993, but now the joke is in worse taste due to the infamous second attack on the towers a mere eight years later in 2001.
Seeing Keenan portraying Don Cornelius collapsing and dying at the end of the spoof of the series called "Old Train" is now this given Cornelius' 2012 suicide.
Hilarious in Hindsight: Jamie Foxx had plenty of opportunities to impersonate Ray Charles, especially since this was the time when Charles was promoting Diet Pepsi. Foxx would later win an Oscar for doing the same thing, albeit in more dramatic fare.
Jamie Foxx also impersonated Garrett Morris (Saturday Night Live's first token black cast member from the show's first five years) in a fake American Express commercial featuring Chris Rock (played by Shawn Wayans) — a couple years before Foxx would appear with Garrett Morris on the WB sitcom The Jamie Foxx Show.
In the MC Hammer-skewering sketch "Too Sold Out to Quit", the joke of Hammer selling out to make himself wealthy ("The rules of being legit/Make a ton of money and then you can quit!") becomes this trope when Hammer ended up more than $10 million in debt the next year.
Fame, it don't last long/Look at Vanilla Ice, he is gone!
There was a sketch called East Hollywood Squares, an urban-ized take on the famous game show. In 2013, MTV 2 debuted Hip-Hop Squares...an urban-ized take on the famous game show.
To quote Jim Carrey's take on Vanilla Ice, "What's your real name? / Robert Van Winkle / Why'd you change it? / Nothing rhymes with Winkle". Except possibly the name of the main villain from Carrey's breakthrough into movie stardom several years later.
The Star Treksketch featured Sulu complaining about how Captain Kirk gets all the girls and he gets none, ending with his enthusiasm at the prospect of getting some. Ohhh myyyyy...
For those who don't know already, there was a time when Jim Carrey (who was credited as his real name "James Carrey" for most of his tenure) was the crazy white guy on In Living Color — and that Jamie Foxx was on this show from season three to the end.
Shawn Wayans initially got his start on the show not as an actor, but as the show's DJ, DJ SW1.
Marlon Wayans was also on this show as a feature player, but only for season three.
Seasonal Rot: Season Four, when the Wayans siblings (Keenan-Ivory, Damon, Kim, Shawn, and Marlon) were kicked off the show following many disputes over censorship, and again in Season Five when Jim Carrey was rarely seen due to his budding movie career.