the only one i can think of is Lucky Star, its humor is heavily based on the 00's otaku culture that people that just got into anime or otaku culture in general might not get any of the references they made at all. not to say that it's not enjoyable for new comers, but a big part of lucky star experience is to spot all the references, and laugh.

unlike video games, i dont think anime really ages, stuff that are considered good back then will still be considered good today if they're actually good. there's a reason why a lot of people are still watching Ghibli movies, praising movies like Akira and Ghost In The Shell, discussing Evangelion, got into shows like Dragon Ball and Sailor Moon. an amazing show will always be an amazing show regardless of time.