Rick Steiner as a heel in the summer of 1999. He even gets PPV matches with Goldberg and Sting. I don't remember anyone giving a crap about him anymore.
I think he and Bischoff were fishing/hunting buddies so that probably helped him but yeah, by 1999 he was over the hill and not really over despite the fact that just a year earlier he was pretty damn popular after the initial Steiners split.
He really did get a strong push upon his return from injury in 99.
Slamboree - Wins the TV title from Booker T then later in the night attacks Goldberg and Sting, ruining the first ever big PPV match between them.
Great American Bash - Beats Sting after Sting gets mauled by dogs for some reason.
Bash at the Beach - Defends his TV title against Van Hammer of all people.
Road Wild - High profile match v Goldberg.
Fall Brawl - Defends his TV title against Perry Saturn.
Halloween Havoc - Beats Chris Benoit to regain the TV title.
Mayhem - Was supposed to have a big US champ v TV champ match v Scott Hall but no-showed the PPV and was stripped of the title and his push ended. Within a month he was in the crappy Varsity Club reunion with Kevin Sullivan and Mike Rotunda.
Also he had a lot of Nitro main events too. I remember that summer feud with Goldberg/Sting/Hogan v Nash/Sid/Steiner he really felt like the odd man out and clearly didn't have the star power of the other 5 guys.