Creator: Fred Barron, Dottie Dartland, Marco Pennette
Years: 1995-1999
I watched this pretty religiously when it came out. I was hooked in by Lea Thompson because, you know, Back to the Future. Then 15 year-old me stayed because of Amy Pietz; I almost wanted to see Cats because of her. But eventually I stayed because of Malcolm Gets, who does a great job of playing Richard, the artist for Caroline’s comic strip. He’s got a sharp wit and evokes pathos with his (at first) unrequited pining for Caroline. Eventually, they end up together, then don’t, then do, ad nauseum. And the supporting cast isn’t terribly funny, so yeah, not watching this again.
Death By Troggles 
Here’s a show that’s all about archetypes at a time when other sitcoms were actually taking risks. Amy Pietz is slutty, which is kind of used as her only real joke most of the time, but they were more daring on Golden Girls. I watched this show a lot, but I don’t remember any of it, which is pretty telling.
Malcolm Gets was my favorite as well, though until I read your description of him, I wouldn’t even have remembered his character.