It seems to me that any artist who falls into the trap of using "hot" pop-culture references or buzzwords of their day, including the latest technology/gadgets, etc -- Will likely not be remembered well or simply looked at by our ancestors like space aliens. I even suspect that the highly acclaimed "Social Network" movie will likely be forgotten just like Myspace once the hype dies out. Our generation goes through trends and memes like water so I assume whatever is hip now will be forgotten or evolved beyond recognition within 10 years.
On the comedy topic, I hate to make this comparison, but Anchorman's Will Ferrell and similar comedians seem to fall into the Eddie Murphy, Mike Myers, Adam Sandler trap of doing the same thing OVER AND OVER AND OVER until all their films look the same and it is only a matter of time before the charm wares off.
It's rare to see an actor or musician simply keep reinventing themselves or stepping out of their comfort level, but those that do seem to last longest or at least disappear into obscurity with style.
Hence: Tyler Perry's Madea will be timeless.