Captain Planet has already been mentioned several times, so I'm throwing in my vote with no further commentary.
George Lopez's self-titled sitcom from the mid 2000s had it's fair share of woke moments.
Here's 2 examples: [1] There's an episode where a racist white guy moves into the neighborhood and puts up statues of sleeping Mexicans with their head buried under their sombreros next to a statue of a donkey. George gets indignant to the point he shouts "viva la raza". He then plotted with his TV-show mother to smash the statuettes in the middle of the night, but never got to, because his previous outburst encouraged his TV-show son to do it instead (while recording himself in the act, no less, also saying "viva la raza"). In the end, the neighbor took the statues down after a sternly-worded letter from the TV-show wife.
[2] There's another episode where a registered sex offender moves into the neighborhood, and it causes George to stir up a lynch mob. They knock on the door, and it turns out to be a woman, everybody goes home. The TV-show wife is righty disturbed by this double standard (with George dismissing her), and after an argument she starts printing flyers offscreen that are implied to have basically said "stay away from this person". The son then asks George how to get girls in what appears to be a side plot, and long story short, the son misinterprets what he is told.
[2 cont.] Next thing we know, the son shows up at the sex offender's house, the situation looking bad for her. However, she is able to explain that the son hopped her fence, took his shirt off, made a provocative statement then pulled out a condom. So George and wife bring him home and ask why the hell he did what he did. First, the aforementioned misinterpretation of what George told him about getting girls, saying he had to be "bold and confident to get a woman" (George says in his own defense he was referring to girls his son's age). Then the son says he saw the flyers the TV-show wife was printing and thought she looked pretty. He gets more of a stern talking to from that point, and the situation is never brought up again in future episodes.
There are also non-woke episodes that aged like milk, like the one that spends more or less its entire runtime shilling for life insurance. It's not all bad, though, there are moments like this that have aged like a fine wine.
The Charmed reboot is horrible on its face (never watched it), but in hindsight it had its foundation laid from the original show (1998-2006). The side plots for a lot of episodes (and main plots for a few) has the girls whoring around and trying to hook up with the nearest lughead they can wrap their arms around frequently. At one point in the series, there is an entire arc that can best be described "The Alyssa Milano Boo-Boo Hour" times however many episodes it lasted until progressing the story. The male main characters are often the ones singled out for bad writing, but not all the time. Overall the show can best be described as "Feminist" in the 2nd-wave sense.
Captain Planet has already been mentioned several times, so I'm throwing in my vote with no further commentary.
George Lopez's self-titled sitcom from the mid 2000s had it's fair share of woke moments.
Here's 2 examples: [1] There's an episode where a racist white guy moves into the neighborhood and puts up statues of sleeping Mexicans with their head buried under their sombreros next to a statue of a donkey. George gets indignant to the point he shouts "viva la raza". He then plotted with his TV-show mother to smash the statuettes in the middle of the night, but never got to, because his previous outburst encouraged his TV-show son to do it instead (while recording himself in the act, no less, also saying "viva la raza"). In the end, the neighbor took the statues down after a sternly-worded letter from the TV-show wife.
[2] There's another episode where a registered sex offender moves into the neighborhood, and it causes George to stir up a lynch mob. They knock on the door, and it turns out to be a woman, everybody goes home. The TV-show wife is righty disturbed by this double standard (with George dismissing her), and after an argument she starts printing flyers offscreen that are implied to have basically said "stay away from this person". The son then asks George how to get girls in what appears to be a side plot, and long story short, the son misinterprets what he is told.
[2 cont.] Next thing we know, the son shows up at the sex offender's house, the situation looking bad for her. However, she is able to explain that the son hopped her fence, took his shirt off, made a provocative statement then pulled out a condom. So George and wife bring him home and ask why the hell he did what he did. First, the aforementioned misinterpretation of what George told him about getting girls, saying he had to be "bold and confident to get a woman" (George says in his own defense he was referring to girls his son's age). Then the son says he saw the flyers the TV-show wife was printing and thought she looked pretty. He gets more of a stern talking to from that point, and the situation is never brought up again in future episodes.
There are also non-woke episodes that aged like milk, like the one that spends more or less its entire runtime shilling for life insurance. It's not all bad, though, there are moments like this that have aged like a fine wine.