The only part that doesn't hold up for me is the typical 90s-sitcom nervous-giggly writing about anything sex-related. The ensemble cast is pure gold, especially Phil and Stephen Root. I still find myself thinking about the cane and quitting-smoking episodes.
The Buttafuoco bit from the second episode. And the episode where Phil is stalked. And the malt liquor bit. And the bit after the jumper with him and Dave Folly lying on the floor.
He was consistently the best part of everything he was in. Even in pretty crap-tastic films like Jingle All the Way, he was still somewhat entertaining.
I remember him being in a very mediocre shooter on the psx called Blasto. The game play was fairly meh. But the one liners were a lot of fun. I bought the game specifically because he was in it.